Acetonitrile → HCID 86757426, compound

Participants

Reaction Steps

3-[5-Amino-7-fluoro-4-methyl-2H-1,4-benzoxazine-3(4H)-on-6-yl]-1-methyl-6-trifluoromethyl-2,4-(1H, 3H)-pyrimidinedione (0.78 g) was mixed with acetonitrile (4 ml), the mixture was slowly added into a flask of −60° C. containing ethyl acrylate (10 ml), acetonitrile (3 ml), CuCl2 (0.35 g) and tert-butylnitrite (0.4 ml). After stirring for 1 hr, the cooling bath was removed and reaction continued for 15 hr. Water (15 ml) and methylene chloride (30 ml) were added and the heavier phase was washed with water (20 ml×3) and then dried over sodium sulfate. After filtration and evaporation, the residue was purified by column chromatography (silica gel, hexane to 25% ethyl acetate) to yield the title compound (0.2 g) as a diastereomeric mixture.

Provenance & Evidence