Dimethylformamide → HCID 86710176, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL sealed tube, 3-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)aniline (1.1 g, 0.0032 mol), (2-((tert-butoxycarbonyl)amino)pyrimidin-5-yl)boronic acid (1.15 g, 0.0048), potassium phosphate (2.04 g, 0.0096 mol), DMF (20 mL) and water (7 mL) were added. The reaction mixture was degassed with N2 for 5-10 minutes. To the same reaction mixture, Pd(PPh3)4 (0.23 g, 0.0002 mol) was added and degassed with N2 for 5-10 minutes. The reaction mixture was stirred at 105° C. for 1 hour. The reaction mass was cooled to room temperature and added ice cold water. The 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 column chromatography (60-120 silica gel, 2% methanol in chloroform) to provide the title compound (1.4 g, 87%). 1H NMR (300 MHz, DMSO-d6): δ 10.42 (s, 1H), 9.47 (s, 1H), 9.02 (d, J=2.4 Hz, 1H), 8.24 (d, J=2.1 Hz, 1H), 7.23 (t, J=7.8 Hz, 1H), 7.07-7.03 (m, 2H), 6.71 (d, J=8.1 Hz, 1H), 5.33 (s, 2H), 4.55 (br s, 4H), 3.83 (t, J=4.8 Hz, 4H), 1.49 (s, 9H). LC-MS (ESI): Calculated mass: 500.2; Observed mass [M+H]+: 501.1 (RT=1.09 min).

Provenance & Evidence