Dioxane (2 mL) was added to a mixture of 2-(4-bromophenyl)pyrimidine (0.59 g, 2.51 mmol, prepared as described in U.S. Pat. No. 5,780,473), tri-t-butylphosphonium tetrafluoroborate (36 mg, 0.12 mmol), and tris(dibenzylideneacetone)dipalladium(0) (57 mg, 0.062 mmol). N-Methyldicyclohexylamine (0.64 mL, 2.99 mmol) and ethyl crotonate (0.62 mL, 4.99 mmol) were added and the mixture was stirred for 18 h at room temperature. The mixture was diluted with ethyl acetate, filtered through a small plug of silica gel which was washed with additional ethyl acetate, and the combined filtrates were concentrated. Purification by chromatography (SiO2, 5:1 hexane/ethyl acetate) provided 0.47 g (70%) of the title compound as an off-white solid. MS 269 (M+H)+.
