Dimethylformamide → HCID 86710179, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL sealed tube, 4-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)-N-cyclo-propylbenzamide (0.15 g, 0.00036 mol), (2-((tert-butoxycarbonyl)amino)pyrimidin-5-yl)boronic acid (0.113 g, 0.00047), potassium phosphate (0.155 g, 0.00072 mol), DMF (10 mL) and water (2 mL) were added. The reaction mixture was degassed with N2 for 5-10 minutes. To the same reaction mixture, Pd(PPh3)4 (0.022 g, 0.000018 mol) was added and degassed with N2 for 5-10 minutes. The reaction mixture was stirred at 95° C. for 1 hour. The reaction mass was cooled to room temperature and added ice cold water. A precipitate was obtained and the solid was collected by filtration. The solid was dissolved in chloroform, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by flash column chromatography (2% methanol in chloroform) to provide the title compound (0.1 g, 48%). 1H NMR (300 MHz, DMSO-d6): δ 10.41 (br s, 1H), 9.47 (s, 1H), 9.19 (d, J=1.8 Hz, 1H), 6.59 (d, J=4.2 Hz, 1H), 8.51 (d, J=1.8 Hz, 1H), 7.98-8.08 (m, 4H), 4.57 (br s, 4H), 3.83 (s, 4H), 2.88-2.89 (m, 1H), 1.48 (s, 9H), 0.73 (d, J=5.4 Hz, 2H), 0.61 (d, J=3.0 Hz, 2H): LC-MS (ESI): Calculated mass: 568.2; Observed mass [M+H]+: 569.2. (RT=1.57 min).

Provenance & Evidence