Ortho-Directed Palladium-Catalyzed Direct C–H Functionalization of 3-Picolinyl- and 3-(2-Cyanoethyl)pyrimidin-4(3H)-ones with Aryl Halides

Abstract

The ortho-directed palladium-catalyzed direct C–H arylation of 3-picolinylpyrimidin-4-one was achieved by using various aryl halides. The method was extended to C–H arylation of pyrimidin-4-ones containing a methoxy group and an aryl group at the C5 site. The 2-cyanoethyl substituent was also evaluated as an ortho-directing group. The method gives access to novel N-substituted 2-aryl or 2,5-diaryl pyrimidin-4-ones. A standard three-step deprotection sequence for the picolinyl group was also studied.