Ethyl Acetate → HCID 66699756, compound

Participants

Reaction Conditions

Reaction Steps

1-(2-(Tetrahydro-2H-pyran-4-yl)ethyl)-6-(trimethylstannyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. 6-Bromo-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (1.00 g, 3.06 mmol), hexamethylditin (1.20 g, 3.67 mmol), tetrakis(triphenylphosphine)palladium(0) (0.71 g, 0.61 mmol), and 1,4-dioxane (10 mL) were combined in a 150 mL sealable vessel with a stirbar. Nitrogen was blown into the vessel to blow out air and the vessel was sealed. The resulting reaction mixture was stirred vigorously and heated at 100° C. for 5 h and then cooled to room temperature. The resulting mixture was diluted with ethyl acetate and filtered through Celite. The filter cake was washed thoroughly with ethyl acetate. The filtrate was concentrated on a rotary evaporator. Flash chromatography (30-60% ethyl acetate in hexane) gave the desired product (783 mg, 62%) as a yellow waxy solid. Rf=0.20 (50% ethyl acetate/hexane); 1H NMR (400 MHz, DMSO-d6) δ 11.84 (s, 1H), 7.88 (s, 1H), 3.87 (t, J=6.64, 2H), 3.80 (dd, J=11.32, 3.12, 2H), 3.18 (t, J=10.93, 2H), 1.60-1.73 (m, 4H), 1.33-1.46 (m, 1H), 1.08-1.23 (m, 2H), 0.31 (s, 9H); MS (ESI) m/z 413[M+1]+.

Provenance & Evidence