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Communication

Single-Step Synthesis of Pyrimidine Derivatives

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Mohammad Movassaghi* and Matthew D. Hill

Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139

J. Am. Chem. Soc., 2006, 128 (44), pp 14254–14255

DOI: 10.1021/ja066405m

Publication Date (Web): October 12, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, movassag@mit.edu

Abstract

We describe a single-step conversion of various N-vinyl and N-aryl amides to the corresponding pyrimidine and quinazoline derivatives, respectively. The process involves amide activation with 2-chloropyridine and trifluoromethanesulfonic anhydride followed by nitrile addition into the reactive intermediate and cycloisomerization. In situ nitrile generation from primary amides allows for their use as nitrile surrogates. The use of this chemistry with sensitive N-vinyl amides and epimerizable substrates in addition to a wide range of functional groups is noteworthy.

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History

Published In Issue November 08, 2006
Received September 4, 2006

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Communication

Single-Step Synthesis of Pyrimidine Derivatives