N,N-Diethylaniline → 5-Chloro-7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5(6H)-one (0.728 g, 2.361 mmol) in phosphoryl trichloride (12 mL, 131.1 mmol) under nitrogen was added N,N-diethylaniline (0.9390 mL, 5.902 mmol). The reaction was then heated to 50° C. for 4 hours. The reaction was concentrated, and the residue obtained was treated with 15 mL of a 1:1 mixture of ice and saturated aqueous sodium bicarbonate. The resulting mixture was extracted with dichloromethane (4×30 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue obtained was triturated with diethyl ether and the solid was collected by means of vacuum filtration. The solid was saved. The filtrate was concentrated and the resulting residue purified by silica gel column chromatography, eluting with 20% methanol in dichloromethane. The product-containing fractions were concentrated under reduced pressure and the material was combined with the triturated solid to afford 5-chloro-7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidine (550 mg, 1.68 mmol, 63% yield). MS (apci) m/z=327.1 (M+H).

Provenance & Evidence