Dimethyl Sulfoxide → Aminocyclopyrachlor-methyl

Participants

Reaction Conditions

Reaction Steps

A 200-mL reactor equipped with a 10-mL jacketed addition funnel below a cold-finger condenser at −10° C., a nitrogen inlet and overhead stirring was charged with tributylamine (20.4 g, 0.11 mol) and DMSO (45 mL). The mixture was stirred at 25° C., and 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid monohydrate (23.1 g, 0.1 mol) was added in portions. The reaction mixture was stirred at 30° C. while bromomethane (13.3 g, 8 mL, 0.14 mol) was condensed into the jacketed addition funnel and then added to the reaction mixture over 30 minutes. The mixture was stirred for an additional 3 h and then added over about 30 minutes to a reactor charged with water (200 mL) at 25° C. The resulting slurry was cooled to 5° C. and filtered. The filtered cake was washed with water (2×30 mL) and dried at 60° C. in a vacuum-oven for 16 h to give 18.4 g (81% yield) of the title compound as an off-white solid melting at 147-148° C.

Provenance & Evidence