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Transition‐Metal‐Free Approach to 4‐Ethynylpyrimidines via Alkenynones
Author(s) -
Golubev Pavel R.,
Pankova Alena S.,
Kuznetsov Mikhail A.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402045
Subject(s) - chemistry , trimethylsilyl , regioselectivity , transition metal , condensation , aryl , acetylene , alkoxy group , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , alkyl , physics , thermodynamics
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 %.
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