Dichloromethane → HCID 73056523, compound

Participants

Reaction Steps

To a 25 mL round bottom flask, tert-butyl (5-(7-(3-(morpholine-4-carboxamido)phenyl)-4-morpholinopyrido[3,2-d]pyrimidin-2-yl)pyrimidin-2-yl)carbamate (0.035 g, 0.00006 mol) and DCM (5 mL) were added. To the same flask, TFA (0.013 g, 0.00012 mol) was added and the mixture stirred at room temperature for 3 hours. The volatiles were evaporated under reduced pressure to provide the crude residue. The crude residue was dissolved in 10% methanol in chloroform and washed with aqueous saturated sodium bicarbonate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by preparative TLC (4% methanol in chloroform, double elution) to provide the title compound (0.015 g, 52%). 1H NMR (400 MHz, DMSO-d6): δ 9.19 (s, 2H), 9.02 (d, J=2.4 Hz, 1H), 8.72 (s, 1H), 8.24 (d, J=2.4 Hz, 1H), 8.04 (t, J=1.6 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.46 (t, J=8.0 Hz, 1H), 7.20 (br s, 2H), 4.52 (br s, 4H), 3.84 (t, J=4.8 Hz, 4H), 3.65 (t, J=4.4 Hz, 4H), 3.48 (t, J=4.8 Hz, 4H): LC-MS (ESI): Calculated mass. 513.2, Observed mass [M+H]+: 514.2 (RT=0.19 min).

Provenance & Evidence