Electrochemical transformation of 5-aminopyrimidin-4(3H)-one: indirect anodic oxidation mediated by electrochemically generated chlorine

Abstract

Anodic oxidation of 5-amino-6-methyl-3-phenylpyrimidin-4(3H)-one 1 conc. HCI–MeOH gave 2-(formamido)-2-methoxy-3-oxobutananilide 2(the crystal structure of which has been determined) and 3-(N-chloroimino)-2-(formamido)-2-methoxybutananilide 3via cleavage of the C(2)–N(3) bond and the migration of C(2) to the 5-amino group by the mediation of electrochemically generated chlorine.