Cesium carbonate → HCID 58532508, compound

Participants

Reaction Steps

To a solution of 3-(4-sec-butyl-phenyl)-2-(4-hydroxy-3,5-dimethyl-phenyl)-3H-pyrido[4,3-d]pyrimidin-4-one (0.25 g, 0.63 mmol) in anhydrous DMF (10 mL) was added cesium carbonate (0.62 g, 1.9 mmol). The color changed to orange. The reaction mixture was stirred at room temperature for 10 minutes under nitrogen. Then, (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (9) (0.300 g, 1.27 mmol) was added and the reaction mixture was stirred at 80° C. for 5 hours under nitrogen, cooled to room temperature, diluted with water (100 mL), and extracted with ethyl acetate (100 mL). The organic phase was washed with water (2×50 mL), then brine (50 mL), and dried over anhydrous Na2SO4. The solvent was evaporated. The crude compound was purified by the Simpliflash system (30% ethyl acetate in hexanes as eluent) to give 2-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,5-dimethyl-phenyl}-3-(4-sec-butyl-phenyl)-3H-pyrido[4,3-d]pyrimidin-4-one (10) as a gummy solid. Yield: 0.20 g (58%).

Provenance & Evidence