UA73735C2 - A method for the preparation of substituted pirimidines (variants) - Google Patents

A method for the preparation of substituted pirimidines (variants) Download PDF

Info

Publication number: UA73735C2
Authority: UA; Ukraine
Prior art keywords: formula; group; haloalkyl; alkyl; substituted
Prior art date: 1999-04-15

Application number

UA2001117794A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Basf Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-04-15

Filing date

2000-10-04

Publication date

2005-09-15

2000-10-04 Application filed by Basf Ag filed Critical Basf Ag

2005-09-15 Publication of UA73735C2 publication Critical patent/UA73735C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 34
238000002360 preparation method Methods 0.000 title abstract description 12
-1 vinylcarbonyl compound Chemical class 0.000 claims abstract description 34
125000005843 halogen group Chemical group 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 15
239000012442 inert solvent Substances 0.000 claims abstract description 13
150000001409 amidines Chemical class 0.000 claims abstract description 11
150000003230 pyrimidines Chemical class 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 26
238000006243 chemical reaction Methods 0.000 claims description 24
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 19
125000001188 haloalkyl group Chemical group 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 12
YCOYDSQEOWWYDT-UHFFFAOYSA-N 3,3-dichloroprop-2-enal Chemical compound ClC(Cl)=CC=O YCOYDSQEOWWYDT-UHFFFAOYSA-N 0.000 claims description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 claims description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical class OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims description 3
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
229950005499 carbon tetrachloride Drugs 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
239000008096 xylene Substances 0.000 claims description 3
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims 4
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
238000003756 stirring Methods 0.000 claims 2
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
238000010438 heat treatment Methods 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 13
238000004587 chromatography analysis Methods 0.000 description 12
239000012074 organic phase Substances 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
150000002170 ethers Chemical class 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000002904 solvent Substances 0.000 description 6
QXQVBEYDHRVIHY-UHFFFAOYSA-N 1,1,1,3-tetrachloro-3-ethoxypropane Chemical compound CCOC(Cl)CC(Cl)(Cl)Cl QXQVBEYDHRVIHY-UHFFFAOYSA-N 0.000 description 4
XFLGYXVBXUAGQV-UHFFFAOYSA-N 4-(trifluoromethyl)benzenecarboximidamide Chemical compound NC(=N)C1=CC=C(C(F)(F)F)C=C1 XFLGYXVBXUAGQV-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000002363 herbicidal effect Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WEJHBEDHLLBJFW-UHFFFAOYSA-N 4-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=C(C(F)(F)F)C=C1 WEJHBEDHLLBJFW-UHFFFAOYSA-N 0.000 description 3
YFSYHLNFYUZGGF-UHFFFAOYSA-N 4-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=C(C(F)(F)F)C=C1 YFSYHLNFYUZGGF-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000003709 fluoroalkyl group Chemical group 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
AGYXIUAGBLMBGV-UHFFFAOYSA-N 3,5-dimethylpyrazole-1-carboximidamide;nitric acid Chemical compound O[N+]([O-])=O.CC=1C=C(C)N(C(N)=N)N=1 AGYXIUAGBLMBGV-UHFFFAOYSA-N 0.000 description 2
PLJCPAJZBGUOCZ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 PLJCPAJZBGUOCZ-UHFFFAOYSA-N 0.000 description 2
GXDPRSMVOOTBNL-UHFFFAOYSA-N 4-chlorobenzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=C(Cl)C=C1 GXDPRSMVOOTBNL-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
FYYLZOKGOFWYEB-UHFFFAOYSA-N acetic acid;4-(trifluoromethyl)benzenecarboximidamide Chemical compound CC([O-])=O.NC(=[NH2+])C1=CC=C(C(F)(F)F)C=C1 FYYLZOKGOFWYEB-UHFFFAOYSA-N 0.000 description 2
BYFGZMCJNACEKR-UHFFFAOYSA-N aluminium(i) oxide Chemical compound [Al]O[Al] BYFGZMCJNACEKR-UHFFFAOYSA-N 0.000 description 2
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical class NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
JRYOZJIRAVZGMV-UHFFFAOYSA-N cyclopropanecarboximidamide;hydron;chloride Chemical compound Cl.NC(=N)C1CC1 JRYOZJIRAVZGMV-UHFFFAOYSA-N 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
FCVKLVNLBIBCCU-UHFFFAOYSA-N hydron;pyrazine-2-carboximidamide;chloride Chemical compound Cl.NC(=N)C1=CN=CC=N1 FCVKLVNLBIBCCU-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007790 solid phase Substances 0.000 description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
BEFIHDBEJKQNKJ-UHFFFAOYSA-N 1-methyl-6-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2h-pyrimidine Chemical compound CN1C(C=2C=CC(=CC=2)C(F)(F)F)N=CC=C1OC1=CC=CC(C(F)(F)F)=C1 BEFIHDBEJKQNKJ-UHFFFAOYSA-N 0.000 description 1
GFYFUMNNRPZKQU-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-4-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound N1=C(C)C=C(C)N1C1=NC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 GFYFUMNNRPZKQU-UHFFFAOYSA-N 0.000 description 1
HKODDOZFJXWWJZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-[3-(trifluoromethyl)phenoxy]pyrimidine 3,3-dichloroprop-2-enal Chemical compound ClC(=CC=O)Cl.ClC1=CC=C(C=C1)C1=NC=CC(=N1)OC1=CC(=CC=C1)C(F)(F)F HKODDOZFJXWWJZ-UHFFFAOYSA-N 0.000 description 1
OKSJFXWTABSDSI-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxypyrimidine Chemical compound CN1N=C(C(F)(F)F)C=C1OC1=CC=NC(C=2C=CC(F)=CC=2)=N1 OKSJFXWTABSDSI-UHFFFAOYSA-N 0.000 description 1
VYLOASWLEVJLKI-UHFFFAOYSA-N 2-(difluoromethoxy)-1h-pyridin-4-one Chemical compound OC1=CC=NC(OC(F)F)=C1 VYLOASWLEVJLKI-UHFFFAOYSA-N 0.000 description 1
ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
VYVZRNTUOWITEO-UHFFFAOYSA-N 3,3-bis[3-(trifluoromethyl)phenoxy]prop-2-enal Chemical compound FC(F)(F)C1=CC=CC(OC(OC=2C=C(C=CC=2)C(F)(F)F)=CC=O)=C1 VYVZRNTUOWITEO-UHFFFAOYSA-N 0.000 description 1
LFRJCVSOTLSQLU-UHFFFAOYSA-N 3,3-dichloroprop-2-enal 4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound ClC(=CC=O)Cl.FC(C=1C=C(OC2=NC(=NC=C2)C2=CC=C(C=C2)C(F)(F)F)C=CC1)(F)F LFRJCVSOTLSQLU-UHFFFAOYSA-N 0.000 description 1
GBMZWWHKLFBHFS-UHFFFAOYSA-N 3,3-dichloroprop-2-enal;2-(4-fluorophenyl)-4-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound ClC(Cl)=CC=O.C1=CC(F)=CC=C1C1=NC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 GBMZWWHKLFBHFS-UHFFFAOYSA-N 0.000 description 1
LFSUOLATOYPNBS-UHFFFAOYSA-N 3-(fluoromethyl)phenol Chemical compound OC1=CC=CC(CF)=C1 LFSUOLATOYPNBS-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
DRNJIKRLQJRKMM-UHFFFAOYSA-N 4-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(C#N)C=C1 DRNJIKRLQJRKMM-UHFFFAOYSA-N 0.000 description 1
FLCYTNZRHAXIPN-UHFFFAOYSA-N 4-[2-(difluoromethoxy)pyridin-4-yl]oxy-2-pyrazin-2-ylpyrimidine Chemical compound C1=NC(OC(F)F)=CC(OC=2N=C(N=CC=2)C=2N=CC=NC=2)=C1 FLCYTNZRHAXIPN-UHFFFAOYSA-N 0.000 description 1
DOPVBZDOHFDAHP-UHFFFAOYSA-N 4-fluorobenzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=C(F)C=C1 DOPVBZDOHFDAHP-UHFFFAOYSA-N 0.000 description 1
JQDATBKJKUWNGA-UHFFFAOYSA-N 4-fluorobenzenecarboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=C(F)C=C1 JQDATBKJKUWNGA-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
KRBLZKALPKHYIC-UHFFFAOYSA-N 5-methyl-4-[3-(trifluoromethyl)phenoxy]-2-[4-(trifluoromethyl)phenyl]pyrimidine Chemical compound CC1=CN=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1OC1=CC=CC(C(F)(F)F)=C1 KRBLZKALPKHYIC-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
NLZUHZJNPQGLLO-UHFFFAOYSA-N [amino-[4-(trifluoromethyl)phenyl]methylidene]azanium;2-sulfanylacetate Chemical compound [O-]C(=O)CS.NC(=[NH2+])C1=CC=C(C(F)(F)F)C=C1 NLZUHZJNPQGLLO-UHFFFAOYSA-N 0.000 description 1
DREXKZUHNNBVGQ-UHFFFAOYSA-N acetic acid;4-fluorobenzenecarboximidamide Chemical compound CC(O)=O.NC(=N)C1=CC=C(F)C=C1 DREXKZUHNNBVGQ-UHFFFAOYSA-N 0.000 description 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
150000004075 acetic anhydrides Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000003851 azoles Chemical class 0.000 description 1
PXXJHWLDUBFPOL-UHFFFAOYSA-O benzamidine(1+) Chemical class NC(=[NH2+])C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-O 0.000 description 1
150000003937 benzamidines Chemical class 0.000 description 1
LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 1
150000008359 benzonitriles Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
150000004891 diazines Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000004995 haloalkylthio group Chemical group 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
125000005311 halosulfanyl group Chemical group 0.000 description 1
230000020169 heat generation Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000003854 isothiazoles Chemical class 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

UA2001117794A 1999-04-15 2000-10-04 A method for the preparation of substituted pirimidines (variants) UA73735C2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US29244299A	1999-04-15	1999-04-15
US33352899A	1999-06-15	1999-06-15
PCT/US2000/009522 WO2000063183A1 (en)	1999-04-15	2000-04-10	Process for the preparation of substituted pyrimidines

Publications (1)

Publication Number	Publication Date
UA73735C2 true UA73735C2 (en)	2005-09-15

Family

ID=26967332

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001117794A UA73735C2 (en)	1999-04-15	2000-10-04	A method for the preparation of substituted pirimidines (variants)

Country Status (22)

Country	Link
EP (1)	EP1200414B1 (de)
JP (1)	JP2002542233A (de)
KR (1)	KR100781851B1 (de)
CN (1)	CN1161342C (de)
AR (1)	AR023506A1 (de)
AT (1)	ATE293608T1 (de)
AU (1)	AU780907B2 (de)
BR (1)	BR0012736A (de)
CA (1)	CA2370285A1 (de)
CO (1)	CO4970700A1 (de)
CZ (1)	CZ20013691A3 (de)
DE (1)	DE60019606T2 (de)
ES (1)	ES2240093T3 (de)
HU (1)	HUP0200830A3 (de)
IL (2)	IL145888A0 (de)
MX (1)	MXPA01010390A (de)
PL (1)	PL351088A1 (de)
PT (1)	PT1200414E (de)
SK (1)	SK285728B6 (de)
UA (1)	UA73735C2 (de)
WO (1)	WO2000063183A1 (de)
ZA (1)	ZA200108392B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2408604A1 (en) *	2000-05-19	2001-11-29	Basf Aktiengesellschaft	Method of combating undesired plant growth on cereals
EA200602045A1 (ru) *	2004-05-19	2007-06-29	Басф Акциенгезельшафт	2-замещённые пиримидины
KR100746582B1 (ko) *	2005-04-19	2007-08-06	주식회사 에이스 디지텍	디스플레이 장치용 광학필터, 이를 포함하는 디스플레이장치, 및 디스플레이 장치용 광학필터의 제조방법
KR100711858B1 (ko) *	2005-04-25	2007-04-30	주식회사 미래건설	세탁물도어를 포함하는 지능형 도어 시스템
CN101171237B (zh)	2005-05-06	2011-04-20	杜邦公司	用于制备任选2-取代的1，6-二氢-6-氧代-4-嘧啶羧酸的方法
AU2006247581B2 (en)	2005-05-16	2011-10-20	E. I. Du Pont De Nemours And Company	Method for preparing substituted pyrimidines
ATE529413T1 (de) *	2005-09-01	2011-11-15	Hoffmann La Roche	Verfahren zur synthese von aryloxydiaminopyrimidinen
CA2626479A1 (en) *	2005-11-03	2007-05-18	Irm Llc	Protein kinase inhibitors
CN106496127B (zh) *	2016-10-21	2019-09-27	苏州大学	一种多取代嘧啶的制备方法
CN106831603B (zh) *	2017-01-09	2019-07-02	辽宁大学	一种含氟嘧啶化合物的制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH660589A5 (de) *	1983-01-28	1987-05-15	Lonza Ag	Verfahren zur herstellung von 2-substituierten 5-nitroso-4,6-diamino-pyrimidinen.
DE3642830A1 (de) *	1986-12-16	1988-07-07	Hoechst Ag	Verfahren zur herstellung von pyrimidinen
DE3642832A1 (de) *	1986-12-16	1988-06-30	Hoechst Ag	Verfahren zur herstellung von aminopyrimidinen
DK160270C (da) *	1988-12-16	1991-08-05	Cheminova Agro As	Fremgangsmaade til fremstilling af 2,4- eller 2,4,5-substituerede 6-hydroxypyrimidiner
CZ290330B6 (cs) *	1995-01-26	2002-07-17	American Cyanamid Company	2,6-Disubstituované pyridinové a 2,4-disubstituované pyrimidinové deriváty, způsob a meziprodukty pro jejich výrobu, jejich pouľití a herbicidní prostředky na jejich bázi a způsob potlačování růstu neľádoucích rostlin
SI0802193T1 (en) *	1996-04-09	2002-02-28	Lonza Ag	Process for the preparation of substituted pyrimidines
CA2275400C (en) *	1997-01-13	2008-07-15	Beat Schmidt	Process for the preparation of substituted pyrimidine desrivatives
BR9815453A (pt) *	1997-03-11	2001-10-23	Du Pont	Composto, composição herbicida e método para controle do crescimento de vegetação indesejada
WO1998056789A1 (en) *	1997-06-10	1998-12-17	E.I. Du Pont De Nemours And Company	Pyrimidinyl azole herbicides

2000
- 2000-04-10 DE DE60019606T patent/DE60019606T2/de not_active Expired - Fee Related
- 2000-04-10 KR KR1020017013141A patent/KR100781851B1/ko not_active Expired - Fee Related
- 2000-04-10 SK SK1475-2001A patent/SK285728B6/sk not_active IP Right Cessation
- 2000-04-10 BR BR0012736-1A patent/BR0012736A/pt not_active Application Discontinuation
- 2000-04-10 HU HU0200830A patent/HUP0200830A3/hu not_active Application Discontinuation
- 2000-04-10 PL PL00351088A patent/PL351088A1/xx not_active Application Discontinuation
- 2000-04-10 MX MXPA01010390A patent/MXPA01010390A/es active IP Right Grant
- 2000-04-10 CA CA002370285A patent/CA2370285A1/en not_active Abandoned
- 2000-04-10 AU AU43371/00A patent/AU780907B2/en not_active Ceased
- 2000-04-10 CZ CZ20013691A patent/CZ20013691A3/cs unknown
- 2000-04-10 IL IL14588800A patent/IL145888A0/xx active IP Right Grant
- 2000-04-10 JP JP2000612275A patent/JP2002542233A/ja not_active Withdrawn
- 2000-04-10 AT AT00923205T patent/ATE293608T1/de not_active IP Right Cessation
- 2000-04-10 CN CNB008079315A patent/CN1161342C/zh not_active Expired - Fee Related
- 2000-04-10 ES ES00923205T patent/ES2240093T3/es not_active Expired - Lifetime
- 2000-04-10 EP EP00923205A patent/EP1200414B1/de not_active Expired - Lifetime
- 2000-04-10 WO PCT/US2000/009522 patent/WO2000063183A1/en not_active Ceased
- 2000-04-10 PT PT00923205T patent/PT1200414E/pt unknown
- 2000-04-13 CO CO00027328A patent/CO4970700A1/es unknown
- 2000-04-14 AR ARP000101750A patent/AR023506A1/es unknown
- 2000-10-04 UA UA2001117794A patent/UA73735C2/uk unknown
2001
- 2001-10-11 IL IL145888A patent/IL145888A/en unknown
- 2001-10-12 ZA ZA200108392A patent/ZA200108392B/xx unknown

Also Published As

Publication number	Publication date
CN1355792A (zh)	2002-06-26
ATE293608T1 (de)	2005-05-15
BR0012736A (pt)	2005-07-05
SK14752001A3 (sk)	2002-05-09
ZA200108392B (en)	2002-12-24
MXPA01010390A (es)	2002-03-27
CZ20013691A3 (cs)	2002-04-17
CA2370285A1 (en)	2000-10-26
ES2240093T3 (es)	2005-10-16
JP2002542233A (ja)	2002-12-10
KR100781851B1 (ko)	2007-12-03
HUP0200830A2 (hu)	2002-07-29
DE60019606T2 (de)	2005-08-18
IL145888A0 (en)	2002-07-25
CN1161342C (zh)	2004-08-11
AU4337100A (en)	2000-11-02
SK285728B6 (sk)	2007-07-06
PL351088A1 (en)	2003-03-24
EP1200414A1 (de)	2002-05-02
EP1200414B1 (de)	2005-04-20
DE60019606D1 (de)	2005-05-25
CO4970700A1 (es)	2000-11-07
HUP0200830A3 (en)	2003-04-28
PT1200414E (pt)	2005-09-30
WO2000063183A1 (en)	2000-10-26
AR023506A1 (es)	2002-09-04
AU780907B2 (en)	2005-04-21
IL145888A (en)	2006-08-20
KR20020000167A (ko)	2002-01-04

Publication	Publication Date	Title
CA2038203C (en)	2001-08-21	Process for the preparation of chlorothiazole derivatives
AU2006278950B2 (en)	2012-06-21	Insecticidal 3-acylaminobenzanilides
AU2009313134B8 (en)	2015-05-28	Novel halogen-substituted compounds
CN108570041A (zh)	2018-09-25	一种含异恶唑啉脲嘧啶类化合物的制备方法
TW209216B (de)	1993-07-11
CN102336743B (zh)	2015-01-14	取代三唑啉酮醚类化合物及其应用
AU780907B2 (en)	2005-04-21	Process for the preparation of substituted pyrimidines
US7799738B2 (en)	2010-09-21	Insecticidal 2-acylaminothiazole-4-carboxamides
JP2946656B2 (ja)	1999-09-06	ウラシル誘導体および除草剤
JP2000204085A (ja)	2000-07-25	イソチアゾ―ルカルボン酸誘導体および病害防除剤
JP2001213869A (ja)	2001-08-07	イソチアゾールカルボン酸誘導体および病害防除剤
US6281358B1 (en)	2001-08-28	Process for the preparation of substituted pyrimidines
JPH0525142A (ja)	1993-02-02	ウラシル誘導体及び有害生物防除剤
JPWO2008035737A1 (ja)	2010-01-28	スルホキシイミノ基を有する４−ニトロベンゾイル誘導体及び水稲用除草剤
CN104045634A (zh)	2014-09-17	含二氟甲基吡唑甲酰胺类化合物及其制备方法和用途
JP6479486B2 (ja)	2019-03-06	４−アルコキシ−５−（トリフルオロメチル）ピリミジン誘導体及びその製造方法
JPH07145137A (ja)	1995-06-06	Ｎ−フェニルカーバメート誘導体およびこれを有効成分とする農園芸用殺菌剤
WO1997000862A1 (en)	1997-01-09	Imino thioether compounds, process for producing the same, intermediate of the same, and bactericide/miticide
JP2002105065A (ja)	2002-04-10	チアゾリルエタノン誘導体及びその製造法
JPH06271525A (ja)	1994-09-27	Ｎ−フェニルカーバメート誘導体およびこれを有効成分とする農園芸用殺菌剤
JPH1029975A (ja)	1998-02-03	セミカルバゾン誘導体及び有害生物防除剤
JP2003146975A (ja)	2003-05-21	イソチアゾール類および病害防除剤
CN101157678A (zh)	2008-04-09	12-磺酰氨基-(15-甲基)-1,15-十五内酯,其制备方法和作为杀菌剂的用途
JP2002105040A (ja)	2002-04-10	オキシム基を有するアクリロニトリル誘導体の製造法