Ethyl Acetate → HCID 59380428, compound

Participants

Reaction Steps

To a stirring and cold (0° C.) solution of methyl (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]acrylate (400 mg, 0.77 mmol, 1 equiv) in THF (10 mL) was added diisobutylaluminum hydride in THF (1M, 3 mL, 3 mmol, 4 equiv). The resulting mixture was stirred at rt for 20 hn and it was then poured into the aq Rochelle's salt solution and EtOAc. This was filtered a pad of Celite®. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were concentrated and residue was triturated with hexane and ether to yield (250 mg, 67% yield). 1H-NMR (DMSO-d6) δ 8.93 (s, 1H), 8.43 (s, 1H), 8.41 (s, 1H), 8.1 (d, 1H), 7.67 (d, 1H), 7.60 (dd, 1H), 7.46 (dd, 1H), 7.39 (m, 1H), 7.24 (m, 2H), 7.17 (d, 1H), 7.10 (m, 1H), 6.49-6.65 (m, 2H), 5.20 (s, 2H), 4.90 (s, 1H), 4.11 (d, 2H); LCMS RT=3.71 min, [M+H]+=492.1.

Provenance & Evidence