Potassium Phosphate, Tribasic → 1-{1-[9-methyl-8-(1H-pyrazol-4-yl)-9H-purin-6-yl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of Pyrazole-4-boronic acid pinacol ester (181 mg, 0.93 mmol) in dioxane (1.5 mL) and water (0.2 mL) were added 1-(1-(8-bromo-9-methyl-9H-purin-6-yl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one (100 mg, 0.23 mmol), Pd(dppf)Cl2 (19 mg, 0.02 mmol), and tribasic potassium phosphate (297 mg, 1.4 mmol). The reaction mixture was heated in a microwave reactor to 180° C. for 60 min. The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to give 60 mg (62.8% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 13.40 (s, 1H), 10.81 (d, 1H), 8.42 (s, 1H), 8.19-8.00 (m, 1H), 7.13 (dd, 1H), 6.99-6.88 (m, 3H), 4.60-4.47 (m, 1H), 3.84 (s, 3H), 3.18 (t, 2H), 2.40-2.25 (m, 2H), 1.80 (t, 2H); MS (EI) for C21H21N9O: 416.4 (MH+).

Provenance & Evidence