Dichloromethane → HCID 19759054, compound

Participants

Reaction Steps

To NaH (240 mg, 5 mmol, 50% in oil, prewashed with pentane) in DMF (5 mL) was added 2-mercaptopyrimidine (5 mmol, 560 mg) in portions over 5 minutes at 0° C. After 30 minutes, 1-(1-chloro-2-hydroxy-3-propanyl)-4-(4,4'-diflurobenzhydryl)piperazine (1.9 g, 5 mmol) in DMF (15 mL) was added over 10 minutes under nitrogen. After 12 days, the sodium chloride was removed by filtration and the DMF was removed in vacuo (~0.5 mm Hg, ~50° C.) to give the crude (1.82 g). Flash column chromatography over silica gel using 2% methanol:methylene chloride (2×) and subsequent washings of the product with pentane gave the pure product (380 mg, 16.7%) as a white solid, mp 75°-76° C.; DCI/MS (M+1)=456; (400 MHz) 1H NMR (CDCl3)δ: 8.55 (s, 1H), 8.50 (s, 1H), 7.35 (m, 4H), 7.0 (m, 4H), 4.2 (s, 1H) , 4.0 (m, 1H), 3.3 (m, 2H), 2.65 (m, 2H), 2.4 (m, 8H).

Provenance & Evidence