Diisopropylethylamine → HCID 58158644, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-fluorophenyl)-6-methyltetrahydropyrimidin-2(1H)-one (240 mg, 1.1 mmol) in tetrahydrofuran (5 mL) was added bis(trichloromethyl) carbonate (170 mg, 0.57 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 (250 mg, 0.76 mmol) in tetrahydrofuran (8 mL) and N,N-diisopropylethylamine (300 mg, 2.3 mmol) were added to the mixture, and the mixture was stirred at room temperature for 1 hr. Ethyl acetate/tetrahydrofuran and saturated aqueous sodium hydrogen carbonate solution were added to the mixture, and the aqueous layer was extracted 3 times with ethyl acetate/tetrahydrofuran. 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=50/50→100/0) to give the title compound (29 mg, 7%) as a white solid.

Provenance & Evidence