Butyl ether → HCID 11582641, compound

Participants

Reaction Steps

2-(3-Fluorophenyl)-2-(4-(5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl amino)piperidin-1-yl)propanenitrile (435 mg, 1 mmol) was dissolved in dry THF (20 mL) and was added 1 M solution of MeMgBr in butyl ether (1.7 mL, 12 mmol) at 0° C. The reaction was stirred at room temperature for 3 h. The mixture was poured into a cold saturated NH4Cl solution (10 mL) and extracted with DCM (2×25 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4 and evaporated under reduced pressure. Purification by silica chromatography (2% MeOH-DCM) afforded the title compound (331 mg, 78%). 1H NMR (400 MHz, CDCl3): δ 7.94 (s, 1H), 7.29-7.21 (m, 3H), 6.83 (t, 1H), 3.81-3.72 (m, 1H), 3.08-3.01 (m, 2H), 2.81 (t, 2H), 2.36-2.20 (m, 4H), 1.96-1.95 (m, 4H), 1.31 (s, 3H), 1.30 (s, 3H). MS (ESI) m/z: Calculated: 424.5; Observed: 425.1 (M++1).

Provenance & Evidence