Boron Trichloride → HCID 59224693, compound

Participants

Reaction Conditions

Reaction Steps

4-(5-Benzyloxy-2-methylphenyl)-6-chloropyrimidin-2-ylamine (12.5 g, 38.4 mmol) obtained in Step 3 above was placed in a reaction vessel, and then dichloromethane (500 ml) was added thereto. The resulting solution was cooled to 0° C. Then, a dichloromethane solution of 1.0 M trichloroborane was added dropwise over 30 minutes. The mixture was stirred at 0° C. for 1 hour, and diluted with dichloromethane (1500 ml). A saturated aqueous sodium bicarbonate solution (2000 ml) was added, and the mixture was warmed to room temperature. The organic layer was separated, and then sequentially washed with water (1500 ml) and a saturated aqueous sodium chloride solution (1000 ml). The aqueous layer was extracted with ethyl acetate (3000 ml), and the ethyl acetate solution was sequentially washed with water (1500 ml) and a saturated aqueous sodium chloride solution (1000 ml). The washed organic layers were combined together, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=2:1) to yield 3-(2-amino-6-chloropyrimidin-4-yl)-4-methylphenol (6.45 g, 71%) as a white solid material.

Provenance & Evidence