1,4-Dioxane → HCID 86710199, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL sealed tube, ((acetyl(3-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)phenyl)carbamoyl)oxy)methyl acetate (0.96 g, 0.0019 mol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.852 g, 0.0038 mol), potassium phosphate tribasic (0.81 g, 0.0038 mol), 1,4-dioxane (45 mL), and water (4 mL) were added. The reaction mixture was degassed with N2 for 5-10 minutes. To the same reaction mixture, Pd(PPh3)4 (0.11 g, 0.000096 mol) was added and the mixture was degassed with N2 for 5-10 min. The reaction mixture was stirred at 82° C. for 30 minutes. The volatiles were evaporated to provide a residue. The residue was dissolved in chloroform. The chloroform layer was washed with water, brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure to provide a crude solid. The crude solid was purified by flash column chromatography (0-2% methanol in chloroform) to provide a solid. The solid was washed with methanol to provide the title compound as a light yellow solid (0.4 g, 40%). 1H NMR (400 MHz, DMSO-d6): δ 9.18 (s, 2H), 9.08 (s, 1H), 8.35 (s, 1H), 7.98 (d, J=8.0 Hz, 1H), 7.91 (br s, 1H), 7.62 (t, J=7.6 Hz, 1H), 7.35 (d, J=7.6 Hz, 1H), 7.20 (br s, 2H), 5.68 (s, 2H), 4.52 (br s, 4H), 3.84 (t, J=4.0 Hz, 4H), 2.57 (s, 3H), 2.06 (s, 3H). LC-MS (ESI): Calculated mass: 558.20; Observed mass [M+H]+: 558.8 (RT: 0.40 min).

Provenance & Evidence