4.7 Article

A One-Pot Synthesis of 2-Aminopyrimidines from Ketones, Arylacetylenes, and Guanidine

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 1, Pages 119-125

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02233

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The three-component reaction of ketones, arylacetylenes, and guanidine catalyzed by the KOBut/DMSO system leads to 2-aminopyrimidines in up to 80% yield. Depending on structure of the starting ketones, the aromatization of intermediate dihydropyrimidifies occurs either with loss of hydrogen molecules or methylbenzenes. The latter process takes place in the ketones, in which one of the substituents is not a methyl group. The reaction conditions are tolerable for dialkyl-, aryl(hetaryl) alkyl-, and cycloalkyl ketones.

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