Bromocyclopentane → HCID 53482367, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-amino-6-(((1S)-1-(7-(methylsulfonyl)-1H-benzimidazol-2-yl)-ethyl)amino)-5-pyrimidinecarbonitrile (110 mg, 0.31 mmol) and cesium carbonate (100 mg, 0.31 mmol) was stirred at rt for 30 min in DMF (2 mL). At this time bromocyclopentane (92 μL, 0.62 mmol) was added. The mixture was stirred at 110° C. in a sealed flask for 18 h. The mixture was cooled to rt and concentrated under reduced pressure. Purification of the residue by flash chromatography over silica gel, using 0 to 10% gradient of MeOH in DCM-EtOAc (1:1) with 0.2% NH4OH as eluent gave 4-amino-6-(((1S)-1-(1-cyclopentyl-4-(methylsulfonyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile: 1H NMR (400 MHz, DMSO-d6) δ 8.09 (1H, s), 7.95 (1H, s), 7.94 (1H, d, J=8.0 Hz), 7.72 (1H, d, J=8.0 Hz), 7.43 (1H, t, J=8.0 Hz), 7.35 (2H, br), 5.93-5.85 (1H, m), 5.03-4.95 (1H, m), 3.54 (3H, s), 2.70-2.66 (1H, m), 2.35-2.32 (1H, m), 2.18-1.94 (6H, m), 1.67 (3H, d, J=8.0 Hz); LC-MS (ESI) m/z 426.1 [M+H]+.

Provenance & Evidence