HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-(6-((6-(2,2-Dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxypyrimidin-4-yl)propanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | Ethyl 3-(6-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxypyrimidin-4-yl)propanoate | HCID 117760192 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(6-((6-(2,2-Dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxypyrimidin-4-yl)propanoic acid | HCID 117760055 | 30.9% |
Reaction Steps
To a solution of ethyl 3-(6-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxypyrimidin-4-yl)propanoate (1.13 g) in methanol (5.0 mL) and THF (10 mL) were added water (5.0 mL) and lithium hydroxide monohydrate (450 mg), and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. 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) to give the title compound (330 mg) as a pale-yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181186B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-f489230ef991457a99e493d63772ae4d |
| Source note | uspto-grants-2015_11 |