BG100366A - Method for the preparation of substitued 4,6-diamino-5-cyanopyrimidines - Google Patents
Method for the preparation of substitued 4,6-diamino-5-cyanopyrimidinesInfo
- Publication number
- BG100366A BG100366A BG100366A BG10036696A BG100366A BG 100366 A BG100366 A BG 100366A BG 100366 A BG100366 A BG 100366A BG 10036696 A BG10036696 A BG 10036696A BG 100366 A BG100366 A BG 100366A
- Authority
- BG
- Bulgaria
- Prior art keywords
- alkalimetallic
- formula
- alkyl
- produced
- diamino
- Prior art date
Links
- BTVHLEVGNAQTBN-UHFFFAOYSA-N 4,6-diaminopyrimidine-5-carbonitrile Chemical class NC1=NC=NC(N)=C1C#N BTVHLEVGNAQTBN-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 150000001768 cations Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical class N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 abstract 2
- UMXIANHOYHXWIQ-UHFFFAOYSA-N (1-amino-2,2-dicyanoethenyl)cyanamide Chemical group N#CNC(N)=C(C#N)C#N UMXIANHOYHXWIQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- -1 2-substituted 4,6-diamino-5-cyanopyrimidines Chemical class 0.000 abstract 1
- SSBDGGIFOJKRTP-UHFFFAOYSA-N 4,6-diamino-2-chloropyrimidine-5-carbonitrile Chemical compound NC1=NC(Cl)=NC(N)=C1C#N SSBDGGIFOJKRTP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07D239/46—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
By the method 2-substituted 4,6-diamino-5-cyanopyrimidines with the formula where R1 means hydrogen, C2-C6-alkyl, C2-C6-alkenyl or C2-C6-alynyl and R2 is hydrogen, C1-C10-alkyl or C3-C6-cycloalkyl, or R1 and R2 together mean radical, q selected from the group -(CH2)3-, -(CH2)4- and -(CH2)5-, are produced as dialkylcyanimidocarbonate having the formula where R3 and C1-C4-alkyl, reacts with the alkalimetallic salts of malononitrile or with malononitrile and alkalimetallic base at temperatures form -10 to 40°C. Alkalimetallic salt of 1-alkoxy-1-cyanamino-2,2-dicyanoethylene is produced having the formula where R3 is C1-C4-alkyl and M+ is alkalimetallic cation. The compound produced reacts with excess ammonia at temperature range from 60 to 100°C, producing alkalimetallic salt of 1-amino-1-cyanamino-2,2-dicyanoethylene with the formula where M+ is alkalimetallic cation. This salt reacts with hydrogen chloride excess in secondary alcohol, water, or a mixture thereof as solvent, where 2-chloro-4,6-diamino-5-cyanopyrimidine is produced reacting with amine having the formula R1R2NH where R1 and R2 have the meanings defined in formula I where the end product is turned out.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9714193A | 1993-07-26 | 1993-07-26 | |
| US21098094A | 1994-03-21 | 1994-03-21 | |
| PCT/EP1994/002312 WO1995003282A2 (en) | 1993-07-26 | 1994-07-14 | Process for the preparation of substituted 4,6-diamino-5-cyanopyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG100366A true BG100366A (en) | 1996-07-31 |
Family
ID=26792702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG100366A BG100366A (en) | 1993-07-26 | 1996-02-19 | Method for the preparation of substitued 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) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255316B1 (en) * | 1997-08-27 | 2001-07-03 | Novartis Animal Health Us, Inc. | Dicyclanil polymorphs and hydrates and their preparation |
| CN102850277A (en) | 2007-04-19 | 2013-01-02 | 日本曹达株式会社 | 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 |
| 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 |
| 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 |
Family Cites Families (3)
| 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 |
| US4783468A (en) * | 1986-04-30 | 1988-11-08 | Ciba-Geigy Corporation | Insecticidal 5-pyrimidine carbonitriles |
-
1994
- 1994-07-14 SK SK103-96A patent/SK10396A3/en unknown
- 1994-07-14 CZ CZ96224A patent/CZ22496A3/en unknown
- 1994-07-14 HU HU9503959A patent/HUT73357A/en unknown
- 1994-07-14 CN CN94192888.8A patent/CN1128024A/en active Pending
- 1994-07-14 AU AU73859/94A patent/AU7385994A/en not_active Abandoned
- 1994-07-14 EP EP94923734A patent/EP0711285A1/en not_active Withdrawn
- 1994-07-14 JP JP7504913A patent/JPH09500632A/en active Pending
- 1994-07-14 BR BR9407024A patent/BR9407024A/en not_active Application Discontinuation
- 1994-07-14 CA CA002166989A patent/CA2166989A1/en not_active Abandoned
- 1994-07-14 WO PCT/EP1994/002312 patent/WO1995003282A2/en not_active Ceased
- 1994-07-25 IL IL11042594A patent/IL110425A0/en unknown
-
1996
- 1996-01-24 FI FI960332A patent/FI960332A0/en not_active Application Discontinuation
- 1996-01-25 NO NO960307A patent/NO960307L/en unknown
- 1996-02-19 BG BG100366A patent/BG100366A/en unknown
- 1996-02-26 LV LVP-96-53A patent/LV11463B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT73357A (en) | 1996-07-29 |
| WO1995003282A3 (en) | 1995-04-13 |
| SK10396A3 (en) | 1996-09-04 |
| WO1995003282A2 (en) | 1995-02-02 |
| HU9503959D0 (en) | 1996-03-28 |
| IL110425A0 (en) | 1994-10-21 |
| EP0711285A1 (en) | 1996-05-15 |
| BR9407024A (en) | 1996-09-10 |
| CA2166989A1 (en) | 1995-02-02 |
| JPH09500632A (en) | 1997-01-21 |
| NO960307D0 (en) | 1996-01-25 |
| AU7385994A (en) | 1995-02-20 |
| LV11463B (en) | 1996-12-20 |
| CN1128024A (en) | 1996-07-31 |
| NO960307L (en) | 1996-01-25 |
| LV11463A (en) | 1996-08-20 |
| FI960332A7 (en) | 1996-01-24 |
| CZ22496A3 (en) | 1996-04-17 |
| FI960332A0 (en) | 1996-01-24 |
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