Methanol → HCID 58826060, compound

Participants

Reaction Steps

To a solution of 5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (1.0 g, 2.5 mmoles) in dichloromethane (80 ml) and pyridine (5 ml) at 0° C. was added chlorotrimethyl silane (3.2 ml, 25.2 mmoles). The mixture was stirred at room temperature for 2.5 hours, then cooled to at 0° C. and butyryl chloride (0.54 ml, 5.2 mmoles) was added. The reaction was stirred at 0° C. for 2.5 hours, and then methanol (20 ml) was added. The reaction was stirred at room temperature for 60 hours. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between dichloromethane and water. The organic phase was separated and washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0.5%, 1% methanol in dichloromethane with 0.1% concentrated ammonium hydroxide aqueous solution) to give crude N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-butyramide and N-[2-butyrylamino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-4-yl]-butyramide, which were loaded on preparative TLC plates separately, eluted with 5% methanol in dichloromethane to give pure N-[2-butyrylamino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-4-yl]-butyramide (145 mgs), M+1: 541, and pure N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-butyramide (425 mgs), MS (M+H)=471.

Provenance & Evidence