Collect. Czech. Chem. Commun. 1986, 51, 215-233

Transformations of substituted 5-aminopyrimidines under conditions of the diazotization

Michal P. Nemeryuka, Andrej L. Sedova, Tamara S. Safonovaa, Antonín Černýb and Jiří Křepelkab

a All-Union Scientific-Research Chemical-Pharmaceutical Institute, Moscow, U.S.S.R.
b Research Institute for Pharmacy and Biochemistry, Prague 3, Czechoslovakia


Reaction of nitrous acid with 4-substituted and 4,6-substituted 5-aminopyrimidines Ia-In produces 4-substituted and 4,5-disubstituted 1,2,3-triazoles IIa-IIv,resp. Under similar conditions, 2,5-diaminopyrimidines XIIa-XIId give N(7)-oxides of 2-amino-4-aralkylthiopyrimido[5,4-d]-1,2,3-triazines XIIIa-XIIId, and 5-amino-4-chloropyrimidines In and X give 2-diazocyanoacetamides XIa and XIb resp. Also described are syntheses of 5-formylaminopyrimidines XVa-XVg from glycine ethyl ester via sodium salt XVI.