2-Bromoethanol → HCID 57961676, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium methoxide (2.4 g, 44 mmol) in N,N-dimethylformamide (80 mL) was treated with 3-aminobenzenethiol (4.6 g, 37 mmol) and stirred at 20° C. for 15 min. The reaction mixture was cooled to 0° C., treated with a solution of 2-bromoethanol (3.4 mL, 48 mmol) in N,N-dimethylformamide (10 mL), and stirred at 0° C. for 15 min and at 20° C. for 1 h. The reaction mixture was treated with potassium carbonate (10 g, 74 mmol) followed by 2,4,5-trichloropyrimidine (5.5 mL, 48 mmol) and heated at 60° C. for 1 h and stirred at 20° C. for 18 h. The reaction mixture was diluted with 4:1 water:brine (1 L) and extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with water (3×300 mL) and brine (100 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to a crude product. This material was purified by flash column chromatography give the desired product (7.8 g, 68%) as a solid. LCMS for C12H12Cl2N3OS (M+H)+: m/z=315.9, 317.9.

Provenance & Evidence