Sodium Carbonate → 2-Chloro-4-(2-methyl-3-furanyl)pyrimidine

Participants

Reaction Steps

2,4-Dichloropyrimidine (1.0 g, 6.71 mmol), 4,4,5,5-tetramethyl-2-(2-methyl-3-furanyl)-1,3,2-dioxaborolane (1.397 g, 6.71 mmol), sodium carbonate (1.067 g, 10.07 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.388 g, 0.336 mmol) were added together in 1,4-dioxane (42 mL) and water (7.00 mL) and the resulting mixture was heated at 85° C. under argon for 4 hours. The reaction mixture was allowed to cool to room temperature, diluted with water and extracted with ethyl acetate (×3). The ethyl acetate layers were combined, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by Biotage SP4 column chromatography eluting with a gradient of 0-30% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound (686 mg, 3.52 mmol, 52.5 yield) as a white solid. LC/MS [M+H]+=195/197.

Provenance & Evidence