Potassium Carbonate → HCID 53482315, compound

Participants

Reaction Steps

A mixture of 4-amino-6-(((1S)-1-(7-(methylsulfonyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile (36 mg, 0.10 mmol), potassium carbonate (21 mg, 0.15 mmol) and 4-fluorobenzyl bromide (15 μL, 0.12 mmol) in DMF (3 mL) was stirred at rt in a sealed flask for 18 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by flash chromatography over silica gel, using 2.5% MeOH in DCM as eluent gave 4-amino-6-(((1S)-1-(1-(4-fluorobenzyl)-4-(methylsulfonyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile: 1H NMR (400 MHz, CDCl3) δ 8.08 (1H, s), 7.88 (1H, d, J=8.0 Hz), 7.44 (1H, d, J=8.0 Hz), 7.31 (1H, t, J=8.0 Hz), 6.93 (4H, t, J=8.0 Hz), 6.19 (1H, t, J=8.0 Hz), 5.80-5.71 (1H, m), 5.52 (1H, d, J=16.0 Hz), 5.50 (1H, d, J=16.0 Hz), 5.31 (2H, br), 3.47 (3H, s), 1.62 (3H, d, J=8.0 Hz); LC-MS (ESI) m/z 466.0 [M+H]+.

Provenance & Evidence