Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Reactant | HCID 86626800 | HCID 86626800 | — |
| Reactant | Jones' reagent | HCID 131709961 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86626801 | HCID 86626801 | — |
Reaction Steps
(2-{[(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-methanol (225 mg) is dissolved in acetone (5 ml), and thereto is added 1.94M Jones reagent (290 μl) under ice-cooling, and the mixture is stirred for 30 minutes. To the reaction solution are added sodium hydrogenesulfite, water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→9:1) to give 2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoic acid (181 mg). MS (m/z): 602/604 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07906517B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-74bc1789e7664773b71c1888f8a71ae1 |
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| Source note | uspto-grants-2011_03 |
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