Ethanol → HCID 59380396, compound

Participants

Reaction Steps

To a suspension of methyl (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino) [1]benzothieno[2,3-d]pyrimidin-7-yl]acrylate (100 mg, 0.19 mmol) in THF (3 vmL) were added ethanol (1 mL) and lithium hydroxide (2 N, 0.5 mL, 1 mmol, 5 equiv). The contents were stirred at rt for 16 h. The mixture was concentrated to dryness and the residue was triturated with ether and ethyl acetate to remove organic impurities. To the solid was added some water and 1N HCl to adjust the pH to ˜6. The solid was filtered and dried to obtain (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]acrylic acid (50 mg, 51%). 1H-NMR (DMSO-d6) δ 9.10 (s, 1H), 8.56 (d, 1H), 8.52 (s, 1H), 8.39 (d, 1H), 7.87 (dd, 1H), 7.74 (d, 1H), 7.42-7.59 (m, 3H), 7.30 (m, 2H), 7.23 (d, 1H), 7.17 (m, 1H), 6.69 (d, 1H), 5.26 (s, 2H); LCMS RT=3.77 min, [M+H]+=506.0.

Provenance & Evidence