反应详情

Ethyl 4-hydroxy-3-methyl-2-(morpholin-4-ylmethyl)thieno[2,3-b]pyridine-5-carboxylate (Preparation 27, 1.47 g) and potassium carbonate (1.21 g) are suspended be in DMF (25 mL). The mixture is warmed until the ester dissolves and iodomethane (0.30 mL) is added. The reaction mixture is allowed to stir at room temperature for 20 h. The mixture is then poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers are washed with brine (2×25 mL), dried (Na2SO4), and partially concentrated. Hexanes are added and the resulting solid is filtered to afford 0.70 g of the title compound as a light yellow solids Physical characteristics. M.p. 172-173° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.41, 4.19, 3.81, 3.65, 3.59, 2.48, 2.46, 1.27; MS (ESI+) m/z 351 (M+H)+. Anal. Found: C, 58.04; H, 6.54; N, 7.77; S, 8.97.

1. dissolutiondissolves
2. extractionextracted with EtOAc (3×100 mL)
3. washThe combined organic layers are washed with brine (2×25 mL)
4. dry with materialdried (Na2SO4)
5. concentrationpartially concentrated
6. additionHexanes are added
7. filtrationthe resulting solid is filtered