Sodium Methoxide → 2-(4-Bromo-3-methylphenyl)pyrimidine

Participants

Reaction Steps

To a solution of 5.0 g (23.46 mmol) of the title compound of Step A in 15 mL of methanol ("MeOH"), 7.94 g (35.2 mmol) of the title compound of Step B and 1.9 g (35.2 mmol) of sodium methoxide were added and the mixture stirred at room temperature under argon for 1 hr. The solution was then refluxed for 4 hrs and concentrated to about 10 mL. The residue was then added to 200 mL of water and extracted with 4×150 mL of ethyl acetate ("EtOAc"). The combined organic extracts were washed once with water and dried and evaporated. The residue was chromatographed on 100 g of silica gel using Hexanes/EtOAc 4:1 to provide 1.65 g (28%) of the title compound of this step as a white solid.

Provenance & Evidence