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

…, NI Protsuk, IA Ushakov, BA Trofimov

Index: Trofimov, Boris A.; Schmidt, Elena Yu.; Zorina, Nadezhda V.; Ivanova, Elena V.; Ushakov, Igor A. Journal of Organic Chemistry, 2012 , vol. 77, # 16 p. 6880 - 6886

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Abstract

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 dihydropyrimidines occurs either with loss of hydrogen molecule or methylbenzenes. The latter process takes place for the ketones, in which one of the substituents is not a methyl group. The reaction conditions ...