Potassium Fluoride → 2-Chloro-4-(1-ethoxyvinyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine

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Reaction Steps

A degased solution of 2,4-dichloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine (7 g, 26.82 mmol), tributyl(1-ethoxyvinyl)stannane (9.51 mL, 28.16 mmol) and bis(triphenylphosphine)-palladium chloride (0.376 g, 0.54 mmol) in dimethylformamide (200 mL) was heated under argon at 100° C. for 1.5 h. The mixture was poured into a solution of potassium fluoride (20 g) in water 250 mL, and the mixture was extracted with MTBE (300 mL). The organic phase was washed with water, dried over sodium sulfate, and filtered through a pad of silica gel. The residue was crystallised from heptane (50 mL) to yield the title compound (4.0 g). The mother liquor was concentrated in vacuum and purified by column chromatography on silica gel, using a gradient of 0-15% ethyl acetate in heptane as eluent to yield additional amount of the title compound (2.9 g), total yield being 6.45 g (81%).

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