Triethylamine → 1-(1-(5-amino-6-(methylamino)pyrimidin-4-yl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Participants

Reaction Steps

To a suspension of 6-chloro-N-methyl-5-nitropyrimidin-4-amine (550 mg, 2.92 mmol) in methanol (11 mL) was added triethylamine (0.55 mL, 3.94 mmol) and 4-(2-keto-1-benzimidazolinyl)piperidine (638 mg, 2.94 mmol). The mixture was stirred at ambient temperature for 1 h and then 10 wt % Pd on C (wet) was added and the mixture was stirred under hydrogen for 1 h. The mixture was diluted with methanol and was filtered through Celite. The filtrate was concentrated and the resulting solid was triturated with a solution of 50% aqueous methanol. The methanol was removed in vacuo and the aqueous slurry was filtered and dried to afford 1-{1-[5-amino-6-(methylamino)pyrimidin-4-yl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one (842 mg, 2.48 mmol, 85% yield) as a peach colored solid. 1H NMR (400 MHz, DMSO-d6): δ 10.86 (s, 1H), 7.82 (s, 1H), 7.43-7.36 (m, 1H), 7.01-6.94 (m, 3H), 6.29 (q, 1H), 4.31 (tt, 1H), 4.20 (s, 2H), 3.50 (br d, 2H), 2.85 (d, 3H), 2.74 (t, 2H), 2.54 (qd, 2H), 1.68 (dd, 2H). MS (EI) for C17H21N7O: 340 (MH+).

Provenance & Evidence