Patent GB-1189188-A (GB)
Title: Aminopyrimidine Derivatives
IPC: C07D239/50
Filed: 1967-11-09
Abstract: 1,189,188. 2-Aminopyrimidine derivatives. DEUTSCHE GOLDUND SILBER SCHEIDEANSTALT. 9 Nov., 1967 [9 Nov., 1966 (2)], No. 50987/67. Heading C2C. Novel 2-aminopyrimidine derivatives of the Formula I wherein X is a nitrogen atom in which case R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> which may be the same or different, are H, halogen, -CF 3 , -CN, -SH, alkyl, alkylthio, alkylsulphonyl, -OH, alkoxy, -NO 2 , -COOH, carbalkoxy, -CONH 2 , alkylcarbamoyl, -NH 2 , alkylamino, optionally substituted phenylamino, acylthio, acyloxy, or acylamino, the acyl group being derived from carbonic acid, aliphatic carbonic acid monoesters, optionally substituted benzoic acids or saturated or unsaturated aliphatic mono- or dicarboxylic acids containing 1 to 6 carbon atoms, carbamic or substituted carbamic acids of the general formula R<SP>7</SP>(R<SP>8</SP>)-N-CO.OH in which R<SP>7</SP> and R<SP>8</SP>, which may be the same or different are alkyl or taken together represent a 5-, 6- or 7-membered ring optionally containing another hetero atom; or X is a CH group, in which case R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> are as defined above except that one of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> must be -NH 2 , alkylamino, or optionally substituted phenylamino or an acylamino group as defined above and if one of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> is -NH 2  in the four position of the pyrimidine ring, the remaining two of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> may be the same or different and may represent any of the radicals or atoms defined above except H or CH 3 ; R<SP>6</SP> is H or acyl of the aforementioned kind; where X is a nitrogen atom no more than five of R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP>, R<SP>5</SP> and R<SP>6</SP> may be hydrogen atoms and acid addition salts thereof are prepared by: (a) Reacting at elevated temperature, optionally in the presence both of an alkaline condensation agent and a solvent, a pyrimidine derivative of the Formula III above with a compound of the Formula IV above in which one of Z and W is NH 2  and the other is halogen or OH. (b) Reacting a compound of one of the formulµ in which M is an alkali metal atom and R is one of the radicals R<SP>1</SP>, R<SP>2</SP> or R<SP>3</SP> with a compound of the general Formula VI above, in an inert solvent at elevated temperatures, optionally in the presence of basic or acidic catalysts, followed by the reduction of an oximino, nitroso or hydroxylamino group, if present, to an amino group. (c) For compounds in which R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are NH 2 , alkylamino, OH, alkoxy, SH, alkylmercapto, or halogen by mutually exchanging the radicals R<SP>1</SP> to R<SP>3</SP> by methods normally employed in pyrimidine chemistry, including hydrolysis, alcoholysis, aminolysis or reaction by means of halogenating agents. (d) By reducing nitro groups in compounds of Formula I above in which one or more radicals R<SP>1</SP> to R<SP>5</SP> are NO 2  groups. (e) Acylating one or more NH 2  groups in the compounds obtained by methods (a) to (d) either successively or at the same time.