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Paper | Regular issue | Vol 96, No. 9, 2018, pp.1549-1569
Published online, 29th August, 2018
DOI: 10.3987/COM-18-13956
Synthesis of 4-Aryl and Unsymmetrical 4,6-Diarylpyrimidines by the Suzuki-Miyaura Cross-Coupling Reaction

Sahaj Gupta, Jennifer A. Melanson, M Selim Hossain, Louis Vaillancourt, Gerald J. Tanoury,* William A. Nugent, and Victor Snieckus*

*Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario K7L 3N6, Canada


A two-step procedure for the synthesis of 4-arylpyrimidines from inexpensive 4,6-dichloropyrimidine via a Suzuki-Miyaura/hydrodechlorination reaction sequence is described. The reaction resulted in the predominant formation of mono-arylated product. The cross-coupling of 4-chloro-6-substituted pyrimidines with various aryl/heteroarylboronic acids also furnished 4,6-disubstituted pyrimidines in acceptable yields.