Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | Potassium bisulfate | HCID 516920 | — |
| Reactant | HCID 67072197 | HCID 67072197 | — |
| Reactant | HCID 67072239 | HCID 67072239 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 21935657 | HCID 21935657 | 107.3% |
Reaction Steps
Within 20 min was dropped 50 ml (60 mmol) of DIBALH (1.2 M solution in toluene) to a dry ice cooled (−30° C.) solution of 6.83 g (20 mmol) 4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine-5-carboxylic acid methyl ester and 4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine-5-carboxylic acid ethyl ester in 100 ml of THF. The reaction was warmed up (0° C. for 1 h) and stirred 1 h at RT. The reaction was cooled (0° C.) and neutralized with KHSO4 solution (10%). The mixture was extracted with ether (3×), the organic phase was washed with a NaCl solution (10%), dried (Na2SO4) and evaporated. The crude product was crystallized (dichloromethane/ether, 0° C.) to give 6.72 g of pure [4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-5-yl]-methanol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07115611B2 |
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| Source dataset | uspto-grants-2006_10 |
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| ORD ID | ord-bfeb831a9fe94004ac68a668b652fdaf |
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| Source note | uspto-grants-2006_10 |
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