IE832926L - Process for the preparation of 2-substituted-5-nitroso-¹4,6-diaminopyrimidines - Google Patents
Process for the preparation of 2-substituted-5-nitroso-¹4,6-diaminopyrimidinesInfo
- Publication number
- IE832926L IE832926L IE292683A IE292683A IE832926L IE 832926 L IE832926 L IE 832926L IE 292683 A IE292683 A IE 292683A IE 292683 A IE292683 A IE 292683A IE 832926 L IE832926 L IE 832926L
- Authority
- IE
- Ireland
- Prior art keywords
- substituted
- nitroso
- salt
- general formula
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 229940058936 antimalarials diaminopyrimidines Drugs 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- -1 2-substituted 5-nitroso-4,6-diamino pyrimidine Chemical class 0.000 abstract 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001409 amidines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 abstract 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 abstract 1
- 150000002826 nitrites Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000007669 thermal treatment Methods 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
- C07D239/48—Two nitrogen 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
- C07D239/46—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)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1. A process for producing 2-substituted 5-nitroso-4,6-diamino pyrimidine of the general formula : see diagramm : EP0115325,P5,F1 wherein R is aryl, alkyl, alkylthio, amino, amino substituted by one or two C1 to C4 alkyl groups, or arylalkyl, which comprises the steps of reacting malonic dinitrile with an amidine or guanidine of the general formula : see diagramm : EP0115325,P5,F2 wherein A is Cl, 1/2 SO4 , HSO4 , NO3 , acetate, or 1/3 PO4 , and R has the meaning stated above, in water or alcohol in an acid milieu and in the presence of a nitrite salt to form the respective amidino or guanidino salt of isonitroso-malonitrile, and converting the salt thus obtained in a manner known per se by thermal treatment in dimethyl formamide or a pyridine base in a basic milieu to produce the respective 2-substituted 5-nitroso-4,6-diamino pyrmidine.
[EP0115325A2]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH48283A CH660589A5 (en) | 1983-01-28 | 1983-01-28 | METHOD FOR PRODUCING 2-SUBSTITUTED 5-NITROSO-4,6-DIAMINO-PYRIMIDINES. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE832926L true IE832926L (en) | 1984-07-28 |
| IE56419B1 IE56419B1 (en) | 1991-07-31 |
Family
ID=4188010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE292683A IE56419B1 (en) | 1983-01-28 | 1983-12-12 | Process for the preparation of 2-substituted 5-nitroso-4,6-diaminopyrimidines |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0115325B1 (en) |
| JP (1) | JPS59141566A (en) |
| CA (1) | CA1241958A (en) |
| CH (1) | CH660589A5 (en) |
| DE (1) | DE3465083D1 (en) |
| DK (1) | DK159681C (en) |
| IE (1) | IE56419B1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH667089A5 (en) * | 1985-12-06 | 1988-09-15 | Lonza Ag | METHOD FOR PRODUCING 2-SUBSTITUTED 5-NITROSO-4,6-DIAMINO-PYRIMIDINES. |
| JPH02225474A (en) * | 1989-01-04 | 1990-09-07 | Lonza Ag | Preparation of 2,4-diamino-6-piperidinyl-pyrimidine- 3-n-oxide |
| US6281358B1 (en) | 1999-04-15 | 2001-08-28 | American Cyanamid Company | Process for the preparation of substituted pyrimidines |
| MXPA01010390A (en) * | 1999-04-15 | 2002-03-27 | Basf Ag | Process for the preparation of substituted pyrimidines. |
| DE10024886A1 (en) * | 2000-05-19 | 2001-11-22 | Henkel Kgaa | Colorant for keratin fibers, especially human hair, contains optionally substituted nitrosopyridine and -pyrimidine compound(s) as coloring component |
| CN119371358A (en) * | 2024-10-22 | 2025-01-28 | 湖南吴赣药业有限公司 | A method for preparing 2,4-diamino-6-hydroxy-5-nitrosopyrimidine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1364734A (en) * | 1963-05-15 | 1964-06-26 | Lumiere Lab | Process for the preparation of acyclic and cyclic derivatives of guanidine |
| DE2651794C2 (en) * | 1976-11-12 | 1982-09-23 | Henkel KGaA, 4000 Düsseldorf | Process for the preparation of 5-nitroso-2,4,6-triaminopyrimidine |
| JPS5818367A (en) * | 1981-07-27 | 1983-02-02 | Kohjin Co Ltd | Preparation of nitrosopyrimidine derivative |
-
1983
- 1983-01-28 CH CH48283A patent/CH660589A5/en not_active IP Right Cessation
- 1983-12-12 IE IE292683A patent/IE56419B1/en not_active IP Right Cessation
-
1984
- 1984-01-17 DK DK19784A patent/DK159681C/en active
- 1984-01-18 CA CA000445565A patent/CA1241958A/en not_active Expired
- 1984-01-24 EP EP84100718A patent/EP0115325B1/en not_active Expired
- 1984-01-24 DE DE8484100718T patent/DE3465083D1/en not_active Expired
- 1984-01-27 JP JP1216784A patent/JPS59141566A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0115325B1 (en) | 1987-07-29 |
| IE56419B1 (en) | 1991-07-31 |
| CA1241958A (en) | 1988-09-13 |
| JPH0549666B2 (en) | 1993-07-26 |
| CH660589A5 (en) | 1987-05-15 |
| DK159681C (en) | 1991-04-29 |
| DK19784D0 (en) | 1984-01-17 |
| DE3465083D1 (en) | 1987-09-03 |
| DK159681B (en) | 1990-11-19 |
| EP0115325A2 (en) | 1984-08-08 |
| JPS59141566A (en) | 1984-08-14 |
| EP0115325A3 (en) | 1984-09-12 |
| DK19784A (en) | 1984-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |