Dimethylformamide → HCID 86710187, compound

Participants

Reaction Steps

To a 25 mL round bottom flask, tert-butyl (5-(7-(3-aminophenyl)-4-morpholinopyrido[3,2-d]pyrimidin-2-yl)pyrimidin-2-yl)carbamate (0.2 g, 0.0004 mol), cyclopropane carboxylic acid (0.041 g, 0.00048 mol) and DMF (8 mL) were added. To the same flask, HATU (0.46 g, 0.0012 mol) and TEA (0.22 mL, 0.0016 mol) were added. The reaction mass was stirred at room temperature for 12 hours. The volatiles were evaporated to dryness under reduced pressure to provide a residue. The residue was stirred with water to provide a solid and the solid was collected by filtration. The solid was washed with diethyl ether to provide the crude product. The crude product was purified by flash column chromatography (1-2% methanol in chloroform) to afford the title compound (0.15 g, 66%). 1H NMR (300 MHz, DMSO-d6): δ 10.42 (br s, 2H), 9.48 (s, 1H), 9.07 (d, J=2.4 Hz, 1H), 8.31 (d, J=1.8 Hz, 1H), 8.20 (s, 1H), 7.47-7.67 (m, 3H), 4.57 (br s, 4H), 3.84 (s, 4H), 1.84-1.80 (m, 1H), 1.49 (s, 9H), 0.85-0.83 (m, 4H): LC-MS (ESI): Calculated mass: 568.2; Observed mass [M+H]+: 569.2 (RT=1.56 min).

Provenance & Evidence