Terminal alkyne-functionalized triazine by Sonogashira coupling: synthesis of a potential cell signalling inhibitor via click chemistry

Introduction of the acetylene group on the 1,3,5-triazine scaffold was studied under various conditions. We describe here a new method to functionalize a triazine ring using Sonogashira coupling between 2-benzylsulfanyl-4,6-dichloro-1,3,5-triazine and trimethylsilylacetylene to give the corresponding 2-benzylsulfanyl-4-chloro-6-(trimethylsilyl)ethynyl-1,3,5-triazine. The latter was then used to obtain phosphoric acid mono-{4-[4-(4-amino-6-benzylsulfanyl-1,3,5-triazin-2-yl)-1,2,3-triazol-1-yl]-phenyl} ester via click chemistry by Huisgen 1,3-dipolar cycloaddition reaction. (c) 2008 Elsevier Ltd. All rights reserved.