Tetrahydrofuran → 4'-{[3-[2-(4-fluorophenyl)-2-hydroxyethyl]-2,4-dioxo-6-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

To a mixture of 4′-{[3-[2-(4-fluorophenyl)-2-oxoethyl]-2,4-dioxo-6-(2,2,2-trifluoroethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (0.9 g), tetrahydrofuran (20 mL) and methanol (20 mL) was added sodium borohydride (0.19 g), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the residue was extracted with ethyl acetate and saturated aqueous ammonium chloride solution. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless oil (0.41 g, 45%).

1. concentrationThe reaction mixture was concentrated
2. extractionthe residue was extracted with ethyl acetate and saturated aqueous ammonium chloride solution
3. washThe ethyl acetate layer was washed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography

ORD-Eintrag

ord-dcfce4c27dcc4fa99c4bf666161b564f

Quelldatensatz

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08501750B2