HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Ethyl 3-cyclopropyl-3-(6-((5-(2-fluoro-5-methoxyphenyl)-4-isobutoxypyridin-2-yl)methoxy)pyrimidin-4-yl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | (5-(2-Fluoro-5-methoxyphenyl)-4-isobutoxypyridin-2-yl)methanol | HCID 117760256 | — |
| Reactant | ethyl 3-cyclopropyl-3-(4-oxo-1H-pyrimidin-6-yl)propanoate | HCID 178471101 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | Ethyl 3-cyclopropyl-3-(6-((5-(2-fluoro-5-methoxyphenyl)-4-isobutoxypyridin-2-yl)methoxy)pyrimidin-4-yl)propanoate | HCID 117760016 | 22.7% |
Reaction Steps
Under a nitrogen atmosphere, to a solution of (5-(2-fluoro-5-methoxyphenyl)-4-isobutoxypyridin-2-yl)methanol (200 mg) and ethyl 3-cyclopropyl-3-(6-hydroxypyrimidin-4-yl)propanoate (155 mg) in toluene (9.4 mL) were added 1,1′-(azodicarbonyl)dipiperidine (264 mg) and tributylphosphine (261 μL), and the mixture was stirred at room temperature for 24 hr. Hexane/ethyl acetate (1:1) was added to the reaction mixture, the resulting precipitate was filtered off, and the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (78 mg) as a colorless amorphous solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181186B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-3ae58888745b4629b6fd9091914b4644 |
| Source note | uspto-grants-2015_11 |