Ethyl 2-(6-fluoro-1h-benzo[d]imidazol-1-yl)-5-nitro-6-(tetrahydro-2h-pyran-4-ylamino)pyrimidine-4-carboxylate → ethyl 5-amino-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-4-carboxylate

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Hydrogenation of ethyl 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-5-nitro-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-4-carboxylate (310 mg, 0.717 mmol) was performed in ethanol, using Pd/C (10%), under a positive pressure of hydrogen. After 10 h, the catalyst was filtered, washed with portions of methylene chloride, and the combined filtrate concentrated to give the desired amine as a white solid (220 mg, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ, ppm: 8.97 (s, 1H), 8.47 (dd, J=2.6, 2.2 Hz, 1H), 7.74 (m, 1H), 7.60 (d, J=8.9 Hz, 2H), 7.16 (m, 1H), 6.74 (d, J=8.3 Hz, 1H), 4.37-4.32 (m, 3H), 3.94 (d, J=10.4 Hz, 2H), 3.55 (t, J=10.4 Hz, 2H), 2.01 (m, 2H), 1.58 (m, 2H), 1.42 (t, J=7.1 Hz, 3H); LCMS (EI) m/z 401 (MH)+.

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