Benzyl Alcohol → 5-(Benzyloxy)-2-[4-(methanesulfonyl)piperazin-1-yl]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 5-iodo-2-[4-(methylsulfonyl)piperazin-1-yl]pyrimidine (25.0 g, 67.9 mmol), benzyl alcohol (125 mL), 1,10-phenanthroline (2.45 g, 20 mol %), and cesium carbonate was added copper (I) iodide (12.9 g, 67.9 mmol) and the reaction heated to 110° C. for 90 minutes then cooled to room temperature. DCM (250 mL) was then added and the insolubles filtered off through a pad of celite. The cake washed with DCM (250 mL) and the DCM filtrates washed with water. The aqueous phase was then back extracted with more DCM (500 mL), the combined DCM extracts washed with brine (500 mL), dried (MgSO4), filtered and concentrated in vacuo to a dark brown sludge. This was then purified by flash chromatography (silica gel, 50% EtOAc/hexanes) to give 5-(benzyloxy)-2-[4-(methylsulfonyl)piperazin-1-yl]pyrimidine as an off white solid (14.2 g, 40.7 mmol, 60%).

Provenance & Evidence