Hexane → HCID 59380506, compound

Participants

Reaction Steps

To a stirred and cold (0° C.) solution of toluene (5 mL) was added trimethyl aluminum in hexane (2M, 0.77 mL, 1.54 mmol, 4 equiv) and stirred for 10 min at 0° C. followed by addition of 1-ethyl piperazine (48 mg, 0.42 mmol, 1.1 equiv). The resulting mixture was stirred for an additional 5 min at 0° C. and then warmed to rt. A suspension of methyl (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]acrylate (200 mg) in toluene was added to the above generated mixture. The resulting mixture were heated at 100° C. for 16 h. after cooled to rt, it poured into a cold mixture (0° C.) of NH4Cl aq solution and EtOAc. The resulting gel-like mixture was filtered through a pad of Celite® and pad was washed with EtOAc. The combined EtOAc layers were dried over MgSO4 and concentrated in vacuo. The residue was carefully triturated with ether to yield a yellow solid (200 mg, 86%). 1H-NMR (DMSO-d6) δ 9.08 (s, 1H), 8.54 (m, 3H), 7.92 (dd, 1H), 7.74 (d, 1H), 7.62 (d, 1H), 7.52 (dd, 1H), 7.45 (m, 2H), 7.32 (m, 2H), 7.24 (d, 1H), 7.17 (m, 1H), 5.28 (s, 2H), 3.74 (m, 2H), 3.58 (m, 2H), 2.35 (m, 6H), 1.0 (t, 3H); LCMS RT=3.03 min, [M+H]+=602.0.

Provenance & Evidence