Isopropanol → 5-Bromo-2-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrimidine

Participants

Reaction Conditions

Reaction Steps

Into a 100-mL sealable pressure flask equipped with a magnetic stirbar was added 5-bromo-2-chloropyrimidine (2.50 g, 12.9 mmol), 4-(2-bromo-5-fluorophenoxy)piperidine hydrochloride (4.00 g, 12.9 mmol), 2-propanol (30 mL) and N,N-diisopropylethylamine (4.50 mL, 25.8 mmol). The vial was sealed and heated to 120° C. for 3 h. The reaction mixture was cooled and poured into a 500 mL separatory funnel containing water (250 mL) and the mixture was extracted with ethyl acetate (3×75 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The resulting oil was recrystallized from diethyl ether/hexanes and cooled to −40° C. to cause precipitation, then filtered through Whatman#1 filter paper to give a beige solid, which was dried overnight on the vacuum pump. MS (ESI, Q+) m/z 432, 434, 437 (M+1 for 2×35Br and 37Br).

Provenance & Evidence