N(1)-, N(3)-, and O-alkylation of 5-cyano- 2-methylsulfanyl-4(3h)-pyrimidinone by 4-substituted ω-Bromoacetophenones in the system acetonitrile-K2CO3

Abstract

Alkylation of 4(3H)-pyrimidinones occurs to give a mixture of N(1)-, N(3)-, and O-alkylation products [1]. Analysis of literature data shows that alkylation with haloacetic esters, chloroacetonitrile, N-benzyl-haloacylamides, 3-bromopropan-1-ol, or ω-bromoacetophenone generally gives just the O- and N(3)-alkylation products. According to our results N(1)-alkylation products have hardly been studied and only discovered and separated with the use of haloalkanes and benzyl halides as alkylating agent [1-4].