Pyrimidine derivatives and related compounds. Part 37. Novel nucleophilic substitutions of 5-bromo-6-methyluracils or 5-bromo-6-bromomethyluracils with aromatic amines

Abstract

Condensation of 1-substituted or 1,3-disubstituted 5-bromo-6-methyluracils (4) and aromatic amines gave the corresponding 6-arylaminomethyluracil derivatives (5). Treatment of 5-bromo-6-bromomethyl-1,3-dimethyluracil (10) with primary aromatic amines gave the corresponding 6-arylidenemethyluracil derivatives (11). Reaction of (10) with N-methylaniline gave 5-bromo-1,3-dimethyl-6-(N-methylanilino)methyluracil (13a), which was further treated with primary aromatic amines to afford (11).