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

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-{1-[9-methyl-8-(1H-pyrazol-4-yl)-9H-purin-6-yl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one (30 mg, 0.07 mmol) in DMF (0.5 mL) were added (bromomethyl)cyclobutane (0.02 mL, 0.18 mmol), and sodium bicarbonate (9 mg, 0.11 mmol). The reaction mixture was heated to 100° C. for 24 hours. The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to give 7 mg (23% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 10.85 (s, 1H), 8.42 (s, 1H), 8.25 (s, 1H), 8.01 (t, 1H), 7.13 (dd, 1H), 6.95-6.90 (m, 3H), 4.62-4.45 (m, 1H), 4.21 (d, 2H), 3.86-3.82 (m, 3H), 2.79 (dt, 1H), 2.40-2.25 (m, 2H), 2.01-1.92 (m, 2H), 1.87-1.70 (m, 6H); MS (EI) for C26H29N9O: 484.5 (MH+).

Provenance & Evidence