Journal of Organic Chemistry 2003-07-11

An efficient synthesis of 2-substituted 6-methylpurine bases and nucleosides by Fe- or Pd-catalyzed cross-coupling reactions of 2,6-dichloropurines.

Michal Hocek, Hana Dvoráková

Index: J. Org. Chem. 68(14) , 5773-6, (2003)

Full Text: HTML

Abstract

Fe-catalyzed cross-coupling reactions of 9-substituted or protected 2,6-dichloropurines with 1 equiv of methylmagnesium chloride gave regioselectively 2-chloro-6-methylpurines in good yields. The same reactions with 3 equiv of methylmagnesium chloride or Pd-catalyzed reactions with trimethylaluminum afforded 2,6-dimethylpurines. The 2-chloro-6-methylpurines underwent another coupling with phenylboronic acid to give 6-methyl-2-phenylpurines. All reactions were perfomed for Bn- and THP-protected purine bases as well as for acyl-protected ribosides and 2-deoxyribosides. After deprotection, free purine bases and nucleosides were obtained.