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Synfacts 2006(12): 1219-1219  
DOI: 10.1055/s-2006-955563
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Regiospecific 3-Arylation of Imidazo[1,2-a ]pyrimidines

Contributor(s): Victor Snieckus, Bärbel Wittel
D. S. Ermolat’ev, V. N. Giménez, E. V. Babaev, E. Van der Eycken*
University of Leuven, Belgium and Moscow State University, Russian Federation
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Publikationsdatum:
22. November 2006 (online)

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Significance

A short, efficient, and regioselective microwave-mediated, Pd(0)-catalyzed arylation of imidazo[1,2-a ]pyrimidines to give 2,3-disubstituted imidazo[1,2-a ]pyrimidines is reported. Electron-poor arylbromides give excellent yields while corresponding electron-rich derivatives afford lower yields of products. Heteroaryl bromides also undergo the coupling reactions, albeit in modest yields. Of the several different conditions (MW and thermal) and Pd(0) sources which were tested, those described above gave the best results. The generality of this method was established by the preparation of a library of 45 2,3-disubstituted imidazo[1,2-a ]pyrimidines.