A regioselective approach to trisubstituted 2 (or 6)-arylaminopyrimidine-5-carbaldehydes and their application in the synthesis of structurally and electronically unique GlambdaC base precursors.
An efficient regioselective synthesis of trisubstituted 2(or 6)-arylaminopyrimidine-5-carbaldehydes has been developed via an S(N)Ar reaction of 2,4,6-trichloropyrimidine-5-carbaldehyde with aniline, methylamine, and alkoxide nucleophiles using a combination of phase-transfer catalysis and more traditional SNAr reaction conditions. We demonstrate that in a few synthetic steps, highly functionalized fused-bicyclic pyrimidine substrates can be accessed from the trisubstituted 2-arylaminopyrimidine-5-carbaldehydes. Furthermore, these fused-bicyclic compounds are readily derivatized using the Suzuki cross-coupling reaction to generate electronically and structurally unique GlambdaC base precursors.
Beingessner
Rachel L
RL
National Institute for Nanotechnology and Department of Chemistry, University of Alberta, 11421 Saskatchewan Drive, Edmonton, Alberta, T6G 2M9, Canada.
Deng
Bo-Liang
BL
Fanwick
Phillip E
PE
Fenniri
Hicham
H
D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D017606:Chlorine Compounds / Q000138:chemical synthesis / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry; D003500:Cyclization; D004583:Electrons; D006868:Hydrolysis; D007097:Imines / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D000588:Amines; D017606:Chlorine Compounds; D003432:Cross-Linking Reagents; D007097:Imines; D009570:Nitriles; D011743:Pyrimidines; C059688:alkoxyl radical