tert-Butanol → HCID 68195282, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(5-bromo-2-(2-methyl-1H-imidazol-1-yl)pyrimidin-4-yl)-N-(4-(methylsulfonyl)benzyl)morpholine-3-carboxamide (100 mg, 0.187 mmol), palladium(II) acetate (4.19 mg, 0.019 mmol), Xantphos (21.61 mg, 0.037 mmol), and potassium phosphate, tribasic (79 mg, 0.374 mmol) in 1,4-dioxane (1 mL) and tert-butanol 0.25 mL was heated to 100° C. in a microwave for 1 hour and then heated again to 100° C. in the microwave for 10 hours. Water was subsequently added to the reaction mixture, which formed a precipitate that was collected by filtration. The solids were washed with water and EtOAc to afford the title compound as an off-white solid (54.2 mg, 63.8%). 1H NMR (400 MHz, DMSO-d6) δ 2.63 (s, 3 H), 3.02-3.13 (m, 1 H), 3.21 (s, 3 H), 3.53-3.64 (m, 1 H), 3.71 (t, J=10.99 Hz, 1 H), 3.98-4.06 (m, 1 H), 4.26 (dd, J=11.24, 3.92 Hz, 1 H), 4.37-4.45 (m, 1 H), 4.65 (dd, J=10.61, 3.79 Hz, 1 H), 5.17-5.37 (m, 2 H), 6.83 (d, J=1.52 Hz, 1 H), 7.59 (d, J=8.34 Hz, 2 H), 7.73 (d, J=1.52 Hz, 1 H), 7.84-7.94 (m, 3 H). ESI-MS m/z [M+H]+ calc'd for C21H22N6O4S, 455.14; found 455.3.

Provenance & Evidence