Acetic Anhydride → n-{4-[3-(4-Chorophenyl)-benzo[c]isoxazol-5-yl]-pyrimidin-2-yl}-acetamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-[3-(4-chlorophenyl)-benzo[c]isoxazol-5-yl]-pyrimidin-2-ylamine in toluene (1.5 mL) at room temperature, was added acetic anhydride (0.5 mL). The mixture was heated at 100° C. for 3 hours. The reaction mixture was diluted with water (6 mL) and the precipitate filtered then washed with toluene (2×6 mL). Purification was achieved by silica gel chromatography (4:1 ethyl acetate/hexane then 2% methanol/dichloromethane), followed by a 5% aqueous sodium bicarbonate wash (1×50 mL) to give the title compound as a yellow solid (12 mg, 30% yield). 1H NMR (500 MHz, d6-DMSO) δ 10.62 (s, 1H), 8.85 (s, 1H), 8.75 (d, 1H), 8.31 (d, 1H), 8.25 (d, 2H), 8.02 (d, 1H), 7.85 (d, 1H), 7.75 (d, 2H), 2.3 (s, 3H) ppm. LC-MS (ES+) m/e=365.13 (M+H).

Provenance & Evidence