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P. R. Golubev, A. S. Pankova, M. A. Kuznetsov

“Transition-Metal-Free Approach to 4-Ethynylpyrimidines via Alkenynones”

Eur. J. Org. Chem. 2014, 3614-3621

DOI: 10.1002/ejoc.201402045

A practical approach to the synthesis of 4-ethynylpyrimidines by the condensation of arylamidines with 2-aryl-1-ethoxy-5-(trimethylsilyl)pent-1-en-4-yn-3-ones has been developed. As these latter ketones are easily accessible from bis(trimethylsilyl)acetylene and arylacetyl chlorides, the regioselective condensation reported herein provides a facile access to both TMS-protected and unprotected 4-ethynylpyrimidines in yields of up to 85%.