WO1995003282A3 - Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines - Google Patents

Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines Download PDF

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Publication number
WO1995003282A3
WO1995003282A3 PCT/EP1994/002312 EP9402312W WO9503282A3 WO 1995003282 A3 WO1995003282 A3 WO 1995003282A3 EP 9402312 W EP9402312 W EP 9402312W WO 9503282 A3 WO9503282 A3 WO 9503282A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkali metal
formula
give
reacting
diamino
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP1994/002312
Other languages
French (fr)
Other versions
WO1995003282A2 (en
Inventor
Jean-Marie Assercq
Heinz Peter Schwemlein
Jeffrey William Perine
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy 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.)
Filing date
Publication date
Priority to BR9407024A priority Critical patent/BR9407024A/en
Priority to EP94923734A priority patent/EP0711285A1/en
Priority to SK103-96A priority patent/SK10396A3/en
Priority to AU73859/94A priority patent/AU7385994A/en
Priority to JP7504913A priority patent/JPH09500632A/en
Priority to PL94312716A priority patent/PL312716A1/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of WO1995003282A2 publication Critical patent/WO1995003282A2/en
Publication of WO1995003282A3 publication Critical patent/WO1995003282A3/en
Priority to FI960332A priority patent/FI960332A0/en
Priority to NO960307A priority patent/NO960307L/en
Anticipated expiration legal-status Critical
Priority to BG100366A priority patent/BG100366A/en
Priority to LVP-96-53A priority patent/LV11463B/en
Ceased legal-status Critical Current

Links

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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50—Three nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

2-substituted 4,6-diamino-5-cyanopyrimidines of formula (I) wherein R1 is hydrogen, C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl and R2 is hydrogen, C1-C10alkyl or C3-C6cycloalkyl or R1 and R2 together are a radical, selected from the group of radicals, consisting of -(CH2)3-, -(CH2)4- and -(CH2)5-, are prepared by a process which comprises reacting a dialkyl cyanimidocarbonate of formula (V), wherein R3 is C1-C4alkyl, with an alkali metal salt of malononitrile or with malononitrile and an alkali metal base, at a temperature of -10 to +40°C, to give a 1-alkoxy-1-cyanomino-2,2-dicyanoethylene alkali metal salt of the formula (IV), wherein R3 is C1-C4alkyl and M+ is an alkali metal cation, reacting this compound with an excess of ammonia at a temperature of 60 to 110°C to give a 1-amino-1-cyanamino-2,2-dicyanoethylene alkali metal salt of formula (II), wherein M+ is an alkali metal cation, reacting this salt with excess hydrogen chloride in a secondary alcohol, water or a mixture thereof as solvent to give 2-chloro-4,6-diamino-5-cyanopyrimidine, and then reacting this compound with an amine of the formula R¿1?R2NH to give the final product.
PCT/EP1994/002312 1993-07-26 1994-07-14 Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines Ceased WO1995003282A2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
PL94312716A PL312716A1 (en) 1993-07-26 1994-07-14 Method of production of subtituted 4,6-diamino-5-cyanopyrimidines
EP94923734A EP0711285A1 (en) 1993-07-26 1994-07-14 Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines
SK103-96A SK10396A3 (en) 1993-07-26 1994-07-14 Process for the preparation of substituted 4,6-diamino-5- -cyanopyrimidines and their intermediates products
AU73859/94A AU7385994A (en) 1993-07-26 1994-07-14 Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines
JP7504913A JPH09500632A (en) 1993-07-26 1994-07-14 Process for producing substituted 4,6-diamino-5-cyanopyrimidines
BR9407024A BR9407024A (en) 1993-07-26 1994-07-14 Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines
FI960332A FI960332A0 (en) 1993-07-26 1996-01-24 Process for preparing substituted 4,6-diamino-5-cyano-pyrimidines
NO960307A NO960307L (en) 1993-07-26 1996-01-25 Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines
BG100366A BG100366A (en) 1993-07-26 1996-02-19 Method for the preparation of substitued 4,6-diamino-5-cyanopyrimidines
LVP-96-53A LV11463B (en) 1993-07-26 1996-02-26 Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US9714193A 1993-07-26 1993-07-26
US21098094A 1994-03-21 1994-03-21
US08/097,141 1994-03-21
US08/210,980 1994-03-21

Publications (2)

Publication Number Publication Date
WO1995003282A2 WO1995003282A2 (en) 1995-02-02
WO1995003282A3 true WO1995003282A3 (en) 1995-04-13

Family

ID=26792702

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/002312 Ceased WO1995003282A2 (en) 1993-07-26 1994-07-14 Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines

Country Status (15)

Country Link
EP (1) EP0711285A1 (en)
JP (1) JPH09500632A (en)
CN (1) CN1128024A (en)
AU (1) AU7385994A (en)
BG (1) BG100366A (en)
BR (1) BR9407024A (en)
CA (1) CA2166989A1 (en)
CZ (1) CZ22496A3 (en)
FI (1) FI960332A0 (en)
HU (1) HUT73357A (en)
IL (1) IL110425A0 (en)
LV (1) LV11463B (en)
NO (1) NO960307L (en)
SK (1) SK10396A3 (en)
WO (1) WO1995003282A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104649982B (en) * 2015-02-26 2016-12-07 齐鲁晟华制药有限公司 A kind of preparation method of Dicyclanil

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4441746B2 (en) * 1997-08-27 2010-03-31 ノバルティス アーゲー Dicyclanyl polymorphs and hydrates and their preparation
EP2138480B1 (en) * 2007-04-19 2011-10-12 Nippon Soda Co., Ltd. Method for production of n-(2-amino-1,2-dicyanovinyl)imidates and method for production of aminoimidazole derivatives
CN102250017A (en) * 2011-06-15 2011-11-23 扬州天和药业有限公司 Synthesizing method of dicyclanil
CN102399193A (en) * 2011-12-15 2012-04-04 连云港市亚晖医药化工有限公司 Preparation method of 4, 6-diamino-2-cyclopropylamino-5-cyanopyrimidine
CN104130197A (en) * 2014-07-29 2014-11-05 华中农业大学 Chemical synthetic method of 2,4,6-triamido-5-cyano pyrimidine
CN107056655B (en) * 2017-01-22 2018-12-04 营口三征新科技化工有限公司 A kind of preparation method of 1-amino-1-cyanoamino-2,2-dicyanoethylene sodium salt
CN106966922B (en) * 2017-03-28 2020-10-27 中国科学院大学 Synthesis method of functional substituted dicyanoethylene compound

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1135913B (en) * 1960-11-08 1962-09-06 Bayer Ag Process for the preparation of 2-methyl-4-amino-5-cyanopyrimidine
US3226424A (en) * 1962-10-03 1965-12-28 Hoffmann La Roche Process for preparing 2-lower alkoxy-1,1-dicyanoethylene and 2-amino-1,1-dicyanoethylene
EP0244360A2 (en) * 1986-04-30 1987-11-04 Ciba-Geigy Ag Substituted pyrimidines

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1135913B (en) * 1960-11-08 1962-09-06 Bayer Ag Process for the preparation of 2-methyl-4-amino-5-cyanopyrimidine
US3226424A (en) * 1962-10-03 1965-12-28 Hoffmann La Roche Process for preparing 2-lower alkoxy-1,1-dicyanoethylene and 2-amino-1,1-dicyanoethylene
EP0244360A2 (en) * 1986-04-30 1987-11-04 Ciba-Geigy Ag Substituted pyrimidines

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
E. ALLENSTEIN, R. FUCHS: "5-Cyan-pyrimidin-Derivate durch Cyclisierung von 1-Cyanamino-2.2-dicyan-aethylen", CHEM. BER., vol. 101, no. 4, 1968, pages 1244 - 1249 *
E. ALLENSTEIN, R. FUCHS: "Ueber 1-Cyanamino-2.2-dicyan-ethylene, N.N'-Dicyan-guanidine und den O-Aethyl-N.N'-dicyan-isoharnstoff", CHEM. BER., vol. 101, no. 4, 1968, pages 1232 - 1243 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104649982B (en) * 2015-02-26 2016-12-07 齐鲁晟华制药有限公司 A kind of preparation method of Dicyclanil

Also Published As

Publication number Publication date
AU7385994A (en) 1995-02-20
CA2166989A1 (en) 1995-02-02
WO1995003282A2 (en) 1995-02-02
BR9407024A (en) 1996-09-10
SK10396A3 (en) 1996-09-04
IL110425A0 (en) 1994-10-21
EP0711285A1 (en) 1996-05-15
LV11463B (en) 1996-12-20
FI960332A7 (en) 1996-01-24
JPH09500632A (en) 1997-01-21
NO960307D0 (en) 1996-01-25
CN1128024A (en) 1996-07-31
HUT73357A (en) 1996-07-29
FI960332A0 (en) 1996-01-24
HU9503959D0 (en) 1996-03-28
LV11463A (en) 1996-08-20
CZ22496A3 (en) 1996-04-17
NO960307L (en) 1996-01-25
BG100366A (en) 1996-07-31

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