A chemoselective aniline-chloropyrimidine coupling in a competing electrophilic environment

A highly chemoselective substitution on 4-amino-6-chloropyrimidine ring system having a competing aldehyde functionality has been realized with anilines which produces 4, 6-diaminopyrimidine-5-carbaldehyde in high yield. The reaction may involve the intermediacy of imines. A variety of aromatic amines participate in this reaction successfully to generate diaminopyrimidine aldehydes in moderate to high yield.