Highly Regioselective C-5 Iodination of Pyrimidine Nucleotides and Subsequent Chemoselective Sonogashira Coupling with Propargylamine

Abstract

An efficient C-5 iodination of pyrimidine-5′-triphosphates and subsequent palladium-catalyzed Sonogashira coupling reaction with propargylamine is described. The iodination reaction is highly regioselective and the coupling reaction is highly chemoselective that furnishes exclusive 5-(3-aminopropargyl)-pyrimidine-5′-triphosphate in good yield with high purity (>99%).

Keywords:

• Regioselective
• chemoselective
• Sonogashira coupling
• non-radioactive probe
• aminopropargyl nucleotides