Methanesulfonyl chloride → HCID 17990097, compound

Participants

Reaction Steps

Methanesulfonyl chloride (0.48 mL, 707 mg, 6.17 mmol, 1.2 equiv.) was added to a suspension of 2-{4-[3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-7-yl}-ethanol (2.4 g, 5.14 mmol, 1 equiv.) in anhydrous DCM (20 mL) at 0° C. The resulting mixture was stirred overnight during which time it was warmed to ambient temperature. The standard aqueous work-up gave Methanesulfonic acid 2-{4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-7-yl}-ethyl ester as a slight yellow solid (2.3 g, 79%). 1H-NMR (CD3OD) δ 8.56 (s, 1H), 8.33 (s, 1H), 7.85 (t, 1H), 7.79 (d, J=2.4 Hz, 1H), 7.55 (d, J=7.9 Hz, 1H), 7.51 (dd, J=2.5, 9.1 Hz, 1H), 7.34 (m, 1H), 7.20 (d, J=8.8 Hz, 1H), 5.27 (s, 2H), 4.35 (t, 2H), 3.19 (s, 3H), 3.15 (m, 3H), 2.97 (m, 1H), 2.17 (m, 2H), 1.81 (m, 2H), 1.54 (m, 1H).; LCMS RT=3.03 min; [M+H]+=545.

Provenance & Evidence