Ethyl Acetate → HCID 59380399, compound

Participants

Reaction Steps

To a solution of 7-bromo-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl][1]benzothieno[2,3-d]pyrimidin-4-amine (5.0 g, 10.0 mmol) in 1,2-dimethoxyethane (50 mL) and water (5.0 mL) were added Pd(PPh3)4 (580 mg, 0.50 mmol, 0.05 equiv), Potassium vinyltrifluoroorate (1.48 g, 11.1 mmol, 1.1 equiv), and sodium carbonate (2.66 g, 25.1 mmol, 2.5 equiv) under nitrogen. The reaction mixture was heated to reflux for 15 hours. The reaction mixture was cooled to rt then poured into a flask contains a mixture of water (100 mL) and EtOAc (100 mL). The resulting mixture was extracted with EtOAc (3×50 mL), dried over sodium sulfate then concentrated in vacuo. The crude material was purified by chromatography (5% EtOAc/hexane) to give an off-white solid (4.84 g, 97%). 1H-NMR (CD3OD) δ 8.72 (d, J=5.4 Hz, 1H), 8.47 (s, 1H), 8.37 (d, J=8.4 Hz, 1H), 8.28 (t, 1H), 8.06 (s, 1H), 7.98 (d, J=7.4 Hz, 1H), 7.81 (d, J=2.7 Hz, 1H), 7.72 (m, 2H), 7.55 (dd, J=2.1, 8.9 Hz, 1H), 7.23 (d, J=8.7 Hz, 1H), 6.89 (m, 1H), 5.97 (d, J=17.6 Hz, 1H), 5.43 (s, 2H), 5.39 (d, J=10.9 Hz, 1H); LCMS RT=3.30 min, [M+H]+=445.10.

Provenance & Evidence