Water → HCID 86626801, compound

HRID 604043Notes

Reaction equation

HRID 604043 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[CH2:26][OH:27])[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.CC(C)=[O:39].OS(O)(=O)=O.O=[Cr](=O)=O.[Na].O>CC(C)=O.C(OCC)(=O)C>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:19]=[CH:18][C:17]=1[C:26]([OH:39])=[O:27])[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 86626800HCID 86626800, compoundHCID 131709961Jones' reagent

Product 1

HCID 86626801HCID 86626801, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(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]+

Workup

  1. temperaturecooling
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→9:1)

Sources & evidence

ORD record
ord-74bc1789e7664773b71c1888f8a71ae1
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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