Trifluoroacetic acid → HCID 57522618, compound

Participants

Reaction Steps

A light suspension of (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide, trifluoroacetic acid (3 g, 11.27 mmol) and sodium bicarbonate (1.893 g, 22.54 mmol) in 39 ml of 2:1 methanol/water at room temperature was treated with 2,4,5-trichloropyrimidine (1.550 ml, 13.52 mmol). The resulting mixture was stirred at room temperature for 2 days, diluted with water (20 ml) and ethyl acetate (30 ml); the separated aqueous phase was extracted with ethyl acetate (4×20 ml) and the combined organic layers were washed with brine (20 ml), dried w/Mg2SO4, filtered and concentrated. The crude product was flash chromatographed (50 mm; 0.5 L 2% methanol in CH2Cl2 to 4% methanol in CH2Cl2) to afford the desired product.

Provenance & Evidence