Hydrochloric Acid → ethyl 3-cyclopropyl-3-(6-((6-(2-fluoro-5-methoxyphenyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)pyridin-3-yl)methoxy)pyrimidin-4-yl)propanoate

Under a nitrogen atmosphere, to a solution of (6-(2-fluoro-5-methoxyphenyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)pyridin-3-yl)methanol (189 mg) and ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoate (174 mg) in THF (2.8 mL) was added 60% sodium hydride (25 mg) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was cooled to 0° C., and neutralized with 1N hydrochloric acid. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane and then methanol/ethyl acetate) to give the title compound (164 mg) as a colorless oil.

1. temperatureThe reaction mixture was cooled to 0° C.
2. extractionThe reaction mixture was extracted with ethyl acetate
3. washthe extract was washed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane

ORD 기록

ord-f71d47b7067045bab9f2c678142fe337

출처 데이터셋

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09181186B2