HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → Ethyl 3-cyclopropyl-3-(6-((6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)methoxy)pyrimidin-4-yl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoate | HCID 117760030 | — |
| Reactant | (6-(2-Fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)methanol | HCID 117760196 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ethyl 3-cyclopropyl-3-(6-((6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)methoxy)pyrimidin-4-yl)propanoate | HCID 117759991 | 75% |
Reaction Steps
Under a nitrogen atmosphere, to a solution of (6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)methanol (379 mg) and ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoate (382 mg) in THF (5.0 mL) was added 60% sodium hydride (65 mg) at 0° C., and the mixture was stirred at room temperature for 5 hr. 1N Hydrochloric acid was added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (489 mg) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181186B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-730f3187f5ba4bc590a2813f151512a8 |
| Source note | uspto-grants-2015_11 |