A chemoselective aniline–chloropyrimidine coupling in a competing electrophilic environment

• Published in: Tetrahedron letters Vol. 49; no. 1; pp. 102 - 105
• Main Authors: Choudhury, Anusuya, Chen, Hongfeng, Nilsen, Christopher N., Sorgi, Kirk L.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 2008; Elsevier
• Subjects: Acid catalyzed coupling; Chemistry; Chemistry, Organic; Chloropyrimidine; Diaminopyrimidines; Physical Sciences; Science & Technology; Acid catalyzed coupling; Chloropyrimidine; Diaminopyrimidines

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 amin...