Dimethylformamide → HCID 136052248, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.14 g), 3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole (0.22 g) and N,N-dimethylformamide (10 mL) was added sodium hydride (0.02 g), and the mixture was stirred at 50° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, washed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To the obtained residue was added 1N aqueous sodium hydroxide solution (50 mL), and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was adjusted to pH 4 with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and dissolved in tetrahydrofuran (10 mL). Tetrabutylammonium fluoride (1.0M tetrahydrofuran solution, 0.6 mL) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.07 g, 37%).

Provenance & Evidence