4,6-Dimethoxy-2-(methylsulfonyl)pyrimidine → 2-Chloro-6-(4,6-dimethoxy-2-pyrimidinyloxy)aniline

Participants

Reaction Conditions

Reaction Steps

Potassium t-butoxide (22.4 g) was added portionwise to stirred, cooled 2-chloro-6-hydroxyaniline hydrobromide (22.5 g) in dimethylformamide (100 ml) under nitrogen. After 10 minutes, 4,6-dimethoxy-2-methylsulphonyl pyrimidine (21.8 g) was added, and the mixture was heated at 80° C. with stirring for 22 hours. After addition to ice/water, the precipitated solid was separated by filtration, washed thoroughly with water, dried and recrystallised from isopropanol yielding 17.5 g of the desired product, mp 84°-86° C. Reduction in volume of the mother liquors gave a further 0.85 g of product, mp 86°-87° C.

Provenance & Evidence