Diisopropylethylamine → HCID 58158599, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one (360 mg, 1.8 mmol) in tetrahydrofuran (5 mL) was added bis(trichloromethyl) carbonate (330 mg, 1.1 mmol), and the mixture was stirred at 70° C. for 3.5 hr. The mixture was cooled to room temperature, a solution of N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (300 mg, 0.92 mmol) in tetrahydrofuran (8 mL) and N,N-diisopropylethylamine (360 mg, 2.8 mmol) were added to the mixture, and the mixture was stirred at room temperature for 30 min. Ethyl acetate/tetrahydrofuran and saturated aqueous sodium hydrogen carbonate solution were added to the mixture, and the aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=40/60→90/10) to give the title compound (250 mg, 49%) as a white solid.

Provenance & Evidence