SU578873A3 - Способ получени 5-фторцитозина - Google Patents

Способ получени 5-фторцитозина

Info

Publication number: SU578873A3
Authority: SU; USSR - Soviet Union
Prior art keywords: temperature; ethoxy; water; ammonia; amino
Prior art date: 1973-09-07

Application number

SU7402057486A

Other languages

English (en)

Russian (ru)

Inventor

Домб Сигмунд

Гейзерманн Вернер

Original Assignee

Ф.Гоффманн-Ля Рош И Ко Аг (Фирма)

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.)

1973-09-07

Filing date

1974-09-06

Publication date

1977-10-30

1974-09-06 Application filed by Ф.Гоффманн-Ля Рош И Ко Аг (Фирма) filed Critical Ф.Гоффманн-Ля Рош И Ко Аг (Фирма)

1977-10-30 Application granted granted Critical

1977-10-30 Publication of SU578873A3 publication Critical patent/SU578873A3/ru

Links

238000000034 method Methods 0.000 title description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 7
239000000047 product Substances 0.000 description 7
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
-1 2-ethoxy Chemical group 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 3
229960004413 flucytosine Drugs 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
BZNJWQYNUWZVBR-UHFFFAOYSA-N Cl(=O)(=O)[P] Chemical compound Cl(=O)(=O)[P] BZNJWQYNUWZVBR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
SLQAJWTZUXJPNY-UHFFFAOYSA-N 2-chloro-5-fluoropyrimidin-4-amine Chemical compound NC1=NC(Cl)=NC=C1F SLQAJWTZUXJPNY-UHFFFAOYSA-N 0.000 description 1
BUVSCQCSEWBHDI-UHFFFAOYSA-N 4-chloro-2-ethoxy-5-fluoropyrimidine Chemical compound CCOC1=NC=C(F)C(Cl)=N1 BUVSCQCSEWBHDI-UHFFFAOYSA-N 0.000 description 1
PKZMNMQCFNJXEH-UHFFFAOYSA-N 5-fluoropyrimidin-4-amine Chemical compound NC1=NC=NC=C1F PKZMNMQCFNJXEH-UHFFFAOYSA-N 0.000 description 1
YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
229960002949 fluorouracil Drugs 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000001180 sulfating effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1

Classifications

- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Saccharide Compounds (AREA)

SU7402057486A 1973-09-07 1974-09-06 Способ получени 5-фторцитозина SU578873A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1289573A CH579057A5 (2)	1973-09-07	1973-09-07

Publications (1)

Publication Number	Publication Date
SU578873A3 true SU578873A3 (ru)	1977-10-30

Family

ID=4387383

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU7402057486A SU578873A3 (ru)	1973-09-07	1974-09-06	Способ получени 5-фторцитозина

Country Status (10)

Country	Link
JP (1)	JPS5050386A (2)
AT (1)	AT331259B (2)
BE (1)	BE819606A (2)
CH (1)	CH579057A5 (2)
DD (1)	DD114263A5 (2)
DE (1)	DE2436149C3 (2)
FR (1)	FR2247457B1 (2)
GB (1)	GB1461184A (2)
NL (1)	NL7410730A (2)
SU (1)	SU578873A3 (2)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4080455A (en) *	1975-12-16	1978-03-21	Taisho Pharmaceutical Company Limited	5-Fluoropyrimidin-4-one compositions
ES2549379T3 (es) *	2008-01-22	2015-10-27	Dow Agrosciences Llc	Derivados de 4-amino5-fluoropirimidina como fungicidas
UA107671C2 (en)	2009-08-07	2015-02-10	Dow Agrosciences Llc	N1-substityted-5-fluoro-2-oxopyrimidinone-1(2h)-carboxamide derivatives
MX2012001622A (es)	2009-08-07	2012-04-11	Dow Agrosciences Llc	Derivados de n1-sulfonil-5-fluoropirimidinona.
UA112284C2 (uk)	2009-08-07	2016-08-25	ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі	Похідні 5-фторпіримідинону
UA106889C2 (uk)	2009-08-07	2014-10-27	ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі	Похідні n1-ацил-5-фторпіримідинону
PT2521452E (pt)	2010-01-07	2015-02-24	Dow Agrosciences Llc	Tiazolo[5,4-d]pirimidinas e a sua utilização como agroquímicos
EP2775842B1 (en)	2011-08-17	2017-10-04	Adama Makhteshim Ltd.	1-substituted-5-fluoro-3,6-dihydro-6-imino-2(1H)-pyrimidinone derivatives as fungicidal agents for use in plant protection
MX2015008444A (es)	2012-12-28	2015-09-23	Dow Agrosciences Llc	Derivados de n-(sustituido)-5-flouro-4-imino-3-metil-2-oxo-3,4-dih idropirimidin-1 (2h)-carboximida.
JP6336480B2 (ja)	2012-12-28	2018-06-06	アダマ・マクテシム・リミテッド	１−（置換ベンゾイル）−５−フルオロ−４−イミノ−３−メチル−３，４−ジヒドロピリミジン−２（１ｈ）−オンの誘導体
AU2013370493B2 (en)	2012-12-28	2017-08-17	Adama Makhteshim Ltd.	N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1 (2H)-carboxylate derivatives
KR102309245B1 (ko)	2012-12-31	2021-10-06	아다마 마켓심 리미티드	살진균제로서의 3-알킬-5-플루오로-4-치환된-이미노-3,4-디히드로피리미딘-2(1h)-온 유도체
EA036389B1 (ru)	2013-12-31	2020-11-03	Адама Мактешим Лтд.	5-фтор-4-имино-3-(алкил/замещенный алкил)-1-(арилсульфонил)-3,4-дигидропиримидин-2(1h)-он и способы их получения
FI3096619T3 (fi)	2013-12-31	2025-09-03	Adama Makhteshim Ltd	Synergistisiä sienituhoaineseoksia sienten torjuntaan viljakasveissa

1973
- 1973-09-07 CH CH1289573A patent/CH579057A5/xx not_active IP Right Cessation
1974
- 1974-07-26 DE DE19742436149 patent/DE2436149C3/de not_active Expired
- 1974-08-09 NL NL7410730A patent/NL7410730A/xx unknown
- 1974-09-05 JP JP10142674A patent/JPS5050386A/ja active Pending
- 1974-09-05 FR FR7430135A patent/FR2247457B1/fr not_active Expired
- 1974-09-05 DD DD18093474A patent/DD114263A5/xx unknown
- 1974-09-06 BE BE148257A patent/BE819606A/xx not_active IP Right Cessation
- 1974-09-06 AT AT720874A patent/AT331259B/de not_active IP Right Cessation
- 1974-09-06 GB GB3901574A patent/GB1461184A/en not_active Expired
- 1974-09-06 SU SU7402057486A patent/SU578873A3/ru active

Also Published As

Publication number	Publication date
DE2436149C3 (de)	1979-06-07
NL7410730A (nl)	1975-03-11
FR2247457A1 (2)	1975-05-09
BE819606A (fr)	1975-03-06
GB1461184A (en)	1977-01-13
CH579057A5 (2)	1976-08-31
DD114263A5 (2)	1975-07-20
DE2436149B2 (de)	1978-10-12
FR2247457B1 (2)	1976-10-22
AT331259B (de)	1976-08-10
ATA720874A (de)	1975-11-15
JPS5050386A (2)	1975-05-06
DE2436149A1 (de)	1975-03-27

Publication	Publication Date	Title
JPS6383079A (ja)	1988-04-13	２−クロル−５−クロルメチルチアゾールの製造法
EP0150996B1 (en)	1988-01-07	Manufacture of heptanoic acid derivatives
JP5686805B2 (ja)	2015-03-18	２，４−ジオキソテトラヒドロフラン−３−カルボキシラートを調製するための方法
JPH09124558A (ja)	1997-05-13	スクシニルコハク酸ジアルキルの調製法
CN109761914B (zh)	2021-03-05	一种制备5-三氟甲基尿嘧啶的方法
CN111100019A (zh)	2020-05-05	N,n-二正丙基-2-丙氧基乙胺及其制备方法与应用
KR100486432B1 (ko)	2005-04-29	5-아미노메틸-2-클로로피리딘의 제조 방법
JPS6025428B2 (ja)	1985-06-18	４‐（ヒドロキシメチル）イミダゾール化合物の製法
CN116239465B (zh)	2024-08-23	一种4,4’-二苯醚二甲酰氯的制备方法
NO153570B (no)	1986-01-06	Fremgangsmaate for fremstilling av 2-isopropylaminopyrimidin
CN114989082B (zh)	2024-06-21	基于i价铜化物和三取代膦协同催化的羟氯喹的高效制备方法
JPS6115862A (ja)	1986-01-23	スクシノコハク酸ジアルキルの製法
JP2567394B2 (ja)	1996-12-25	６−ｎ−ベンジルアミノ−９−ベンジルプリン類の製造法
US6274732B1 (en)	2001-08-14	Process for the preparation of 1-[(cyclopent-3-en-1-yl)-methyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
JP2849325B2 (ja)	1999-01-20	４−ハロ−５−（ヒドロキシメチル）イミダゾール化合物の合成方法
KR900001075B1 (ko)	1990-02-26	알킬트리플루오로아세토 아세테이트의 제조방법
CN106432095B (zh)	2019-04-16	匹莫苯丹关键中间体6-(3,4-二氨基苯基)-5-甲基-4,5-二氢哒嗪-3(2h)-酮的制备
JP2001516364A (ja)	2001-09-25	２，６−ジクロロ−５−フルオロニコチノニトリルの製造方法、及び化合物３−シアノ−２−ヒドロキシ−５−フルオロピリド−６−オン−ナトリウム塩とその互変異性体
JPH06199809A (ja)	1994-07-19	２，５−ジブロモピリミジンの製造法
KR20250173705A (ko)	2025-12-11	2-플루오로페닐 2-옥소에틸 말로노나이트릴을 제조하는 방법
SU763339A1 (ru)	1980-09-15	Способ получени 4-амино-5-нитро- 6-метиламинопиримидина
JP2964160B2 (ja)	1999-10-18	シクロプロパンカルボン酸の単離方法及びその中間体の製造方法
US3631101A (en)	1971-12-28	P - (p - (thionylamino)benzamido)benzoyl chloride and its hci addition product
CN118307481A (zh)	2024-07-09	一种嘧霉胺的制备方法
CN117402118A (zh)	2024-01-16	一种瑞舒伐他汀钙中间体的制备方法