IE49709B1 - Pyrimidine derivatives - Google Patents
Pyrimidine derivativesInfo
- Publication number
- IE49709B1 IE49709B1 IE865/80A IE86580A IE49709B1 IE 49709 B1 IE49709 B1 IE 49709B1 IE 865/80 A IE865/80 A IE 865/80A IE 86580 A IE86580 A IE 86580A IE 49709 B1 IE49709 B1 IE 49709B1
- Authority
- IE
- Ireland
- Prior art keywords
- pyrimidine
- isopropylamino
- general formula
- hydroxy
- pyrimidine derivatives
- Prior art date
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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
Abstract
Compounds of the general formula A4=H or OH A5=H or OH A6=H or OH A4=A5=A6=H excluded are prepared by reducing compounds of the general formula A'4=H, alkoxy or aralkyloxy A'5=H, alkoxy or aralkyloxy A'6=H, alkoxy or aralkyloxy A'4=A'5=A'6=H excluded with hydrogen in the presence of a hydrogenation catalyst, e.g. palladium. The compounds I are of therapeutical interest.
Description
The invention relates to a method for the preparation of hydroxy derivatives of 2-isopropylamino-pyrimidine of the general formula I
wherein each of A^, Ag and Ag independently represents a hydrogen atom or a hydroxy group with the proviso that at least one of A4, and Ag and Ag does not represent a hydrogen atom. These compounds are claimed per se in our copending Application No. +77/80, and are of therapeutical interest.
The invention provides a method for the preparation of hydroxy derivatives of 2-isopropylamino-pyrimidine of the general formula I as above defined, the method comprising treating halogeno derivatives of 2-isopropylamino-pyrimidine of the general formula II
wherein each of A'4, A'g and Α'θ independently represents a hydrogen or halogen atom with the proviso that at least one of A'^, A'g and A'g does not represent a hydrogen atom with a mineral base in water at from 100°C to 150°C in the presence of copper.
The invention is illustrated by the following Examples.
EXAMPLE 1;
2-isopropylami no-5-hydroxy-pyrimi di ne Into a one litre reactor were poured 80 ml of water, g of sodium hydroxide, some copper powder and 4.3 g (0.02 mol) of 2-isopropylamino-5-bromo-pyrimidine; the reaction mixture was maintained at 130°C to 135°C for 1 hour under stirring and then at 130°C to 140°C for about 12 hours, also under stirring.
After filtration off of the copper, the reaction mixture was extracted twice with chloroform. The combined extracts were acidified with acetic acid to pH 6.5 to 7.0. The solution was then saturated with sodium chloride causing precipitation of the product, which was collected and washed with water and then with pentane.
The product was then taken up in diethyl ether and treated with carbon black. The solution was concentrated, causing reprecipitation of the product which was collected and recrystallised from water or from isopropyl acetate. The crystals were dried to give 2.45 g (yield 80%) of 2-i'sopropylamino-5-hydroxy-pyrimidine. Elemental analysis showed the expected empirical fonnula CyH^NgO. The
40709
2-isopropylamino-5-bromo-pyrinridine starting material had been readily obtained by reacting, in stoichiometric proportions, 2-isopropylamino-pyrimidine and N-bromo-succinimide in the presence of acetic acid (yield 84%).
EXAMPLE 2:
2-isopropylamino-4-hydroxy-pyrimidine
The method described in Example 1 was repeated except that 2-isopropylamino-4-chloro-pyrimidine was used instead of 2-isopropylamino-5-bromo-pyrimidine. Yield was 77% of a white crystalline product melting at 140°C (Tottoli), elemental analysis of which showed a good correspondence with the formula CyH^NgO. Structural analysis (U.V. Spectrum) confirmed the position of the hydroxy group.
EXAMPLE 3:
2-i sopropylami no-4,6-di hydroxy-pyrimi di ne
The method described in Example 1 was repeated except that
2-isopropylamino-4,6-dichloro-pyrimidine was used instead of 2-isopropylamino-5-bromo-pyrimidine. Yield was 73% of a white crystalline product melting at 221-225°C (Tottoli) with decomposition, elemental analysis of which showed good correspondence with the formula CyH^Oj, HCl. Structural analysis (U.V. Spectrum) confirmed the positions of the hydroxy groups.
Claims (3)
- I. A method for the preparation of a hydroxy derivative of 2-isopropylamino-pyrimidine of the general formula I as herein defined, the method comprising treating a halogeno derivative of 5 2-isopropylamino-pyrimidine of the general fonnula II as herein defined with a mineral base in water at from 100°C to 150°C in the presence of copper.
- 2. A method for the preparation of a hydroxy derivative of 2-isopropylamino-pyrimidine of the general formula I as herein 10 defined, the method being substantially as described herein with reference to any one of the Examples.
- 3. 2-isopropylamino-pyrimidine of general formula I whenever prepared by the method claimed in either of the preceding claims.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7914987 | 1979-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE800865L IE800865L (en) | 1980-10-30 |
| IE49709B1 true IE49709B1 (en) | 1985-11-27 |
Family
ID=10504858
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE865/80A IE49709B1 (en) | 1979-04-30 | 1980-04-28 | Pyrimidine derivatives |
| IE864/80A IE49591B1 (en) | 1979-04-30 | 1980-04-28 | Pyrimidine derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE864/80A IE49591B1 (en) | 1979-04-30 | 1980-04-28 | Pyrimidine derivatives |
Country Status (26)
| Country | Link |
|---|---|
| JP (2) | JPS55145671A (en) |
| AR (2) | AR222870A1 (en) |
| AT (2) | AT380013B (en) |
| BE (2) | BE882593A (en) |
| CH (2) | CH645361A5 (en) |
| DK (2) | DK183780A (en) |
| EG (2) | EG14284A (en) |
| ES (2) | ES491000A0 (en) |
| FI (2) | FI66358C (en) |
| FR (2) | FR2455588A1 (en) |
| GB (2) | GB2055801B (en) |
| HK (2) | HK55683A (en) |
| IE (2) | IE49709B1 (en) |
| IN (2) | IN154067B (en) |
| IT (2) | IT1141296B (en) |
| LU (2) | LU82332A1 (en) |
| MA (1) | MA18824A1 (en) |
| MX (2) | MX5878E (en) |
| MY (2) | MY8400204A (en) |
| NL (2) | NL8002271A (en) |
| NO (2) | NO154055C (en) |
| NZ (2) | NZ193421A (en) |
| OA (2) | OA06527A (en) |
| PT (2) | PT71154A (en) |
| SG (2) | SG22583G (en) |
| ZA (2) | ZA801958B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63145595U (en) * | 1987-03-13 | 1988-09-26 | ||
| JPS645795U (en) * | 1987-06-26 | 1989-01-13 | ||
| JPH01100695U (en) * | 1987-12-21 | 1989-07-06 | ||
| HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
| US5264435A (en) * | 1988-12-29 | 1993-11-23 | Mitsui Petrochemical Industries, Ltd. | Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines |
-
1980
- 1980-04-02 ZA ZA00801958A patent/ZA801958B/en unknown
- 1980-04-02 BE BE0/200083A patent/BE882593A/en not_active IP Right Cessation
- 1980-04-02 BE BE0/200084A patent/BE882594A/en not_active IP Right Cessation
- 1980-04-02 ZA ZA00801960A patent/ZA801960B/en unknown
- 1980-04-03 LU LU82332A patent/LU82332A1/en unknown
- 1980-04-03 FI FI801083A patent/FI66358C/en not_active IP Right Cessation
- 1980-04-03 LU LU82333A patent/LU82333A1/en unknown
- 1980-04-03 FI FI801084A patent/FI66359C/en not_active IP Right Cessation
- 1980-04-07 IN IN254/DEL/80A patent/IN154067B/en unknown
- 1980-04-07 IN IN253/DEL/80A patent/IN154066B/en unknown
- 1980-04-08 CH CH269080A patent/CH645361A5/en not_active IP Right Cessation
- 1980-04-08 CH CH268980A patent/CH645633A5/en not_active IP Right Cessation
- 1980-04-11 NZ NZ193421A patent/NZ193421A/en unknown
- 1980-04-11 NZ NZ193422A patent/NZ193422A/en unknown
- 1980-04-15 GB GB8012351A patent/GB2055801B/en not_active Expired
- 1980-04-15 GB GB8012349A patent/GB2054556B/en not_active Expired
- 1980-04-18 NL NL8002271A patent/NL8002271A/en unknown
- 1980-04-18 NL NL8002272A patent/NL8002272A/en not_active Application Discontinuation
- 1980-04-22 IT IT21543/80A patent/IT1141296B/en active
- 1980-04-22 IT IT21542/80A patent/IT1141487B/en active
- 1980-04-22 MA MA19019A patent/MA18824A1/en unknown
- 1980-04-24 AT AT0221680A patent/AT380013B/en not_active IP Right Cessation
- 1980-04-24 AT AT0221580A patent/AT380012B/en not_active IP Right Cessation
- 1980-04-25 AR AR280811A patent/AR222870A1/en active
- 1980-04-25 AR AR280810A patent/AR222869A1/en active
- 1980-04-28 JP JP5557580A patent/JPS55145671A/en active Granted
- 1980-04-28 NO NO801234A patent/NO154055C/en unknown
- 1980-04-28 IE IE865/80A patent/IE49709B1/en unknown
- 1980-04-28 MX MX808786U patent/MX5878E/en unknown
- 1980-04-28 PT PT71154A patent/PT71154A/en unknown
- 1980-04-28 MX MX808783U patent/MX6514E/en unknown
- 1980-04-28 NO NO801235A patent/NO154056C/en unknown
- 1980-04-28 IE IE864/80A patent/IE49591B1/en unknown
- 1980-04-28 JP JP5557480A patent/JPS55145670A/en active Granted
- 1980-04-28 PT PT71155A patent/PT71155A/en unknown
- 1980-04-29 DK DK183780A patent/DK183780A/en unknown
- 1980-04-29 ES ES491000A patent/ES491000A0/en active Granted
- 1980-04-29 ES ES490999A patent/ES8103060A1/en not_active Expired
- 1980-04-29 DK DK183880A patent/DK183880A/en unknown
- 1980-04-29 EG EG257/80A patent/EG14284A/en active
- 1980-04-29 EG EG258/80A patent/EG14259A/en active
- 1980-04-30 FR FR8009732A patent/FR2455588A1/en active Granted
- 1980-04-30 FR FR8009733A patent/FR2455589A1/en active Granted
- 1980-04-30 OA OA57103A patent/OA06527A/en unknown
- 1980-04-30 OA OA57101A patent/OA06525A/en unknown
-
1983
- 1983-04-28 SG SG225/83A patent/SG22583G/en unknown
- 1983-04-28 SG SG222/83A patent/SG22283G/en unknown
- 1983-11-17 HK HK556/83A patent/HK55683A/en unknown
- 1983-11-17 HK HK555/83A patent/HK55583A/en unknown
-
1984
- 1984-12-30 MY MY204/84A patent/MY8400204A/en unknown
- 1984-12-30 MY MY203/84A patent/MY8400203A/en unknown
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