Water → HCID 86626800, compound

HRID 604042Notes

Reaction equation

HRID 604042 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[CH2:19][OH:20].[Br:30][C:31]1[CH:32]=[N:33][C:34](Cl)=[N:35][CH:36]=1.C(N(CC)C(C)C)(C)C.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=1)[CH2:6][N:7]([CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[CH:12]=[CH:11][C:10]=1[CH2:19][OH:20])[C:34]1[N:35]=[CH:36][C:31]([Br:30])=[CH:32][N:33]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 86626799HCID 86626799, compound

Product 1

HCID 86626800HCID 86626800, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

{2-[(3,5-Bis-trifluoromethyl-benzylamino)-methyl]-4-trifluoromethyl-phenyl}-methanol (7.0 g) is dissolved in toluene (70 ml) and thereto are added 5-bromo-2-chloro-pyrimidine (4.7 g) and N,N-diisopropylethylamine (4.23 ml) and the mixture is heated under reflux for 3 days. The reaction solution is cooled to room temperature, and thereto are added 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 (hexane:ethyl acetate=4:1→13:2) to give (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-methanol (7.37 g). MS (m/z): 588/590 [M+H]+

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 days
  3. customthe mixture is separated
  4. washthe organic layer is washed with a saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→13:2)

Sources & evidence

ORD record
ord-7a37c02a6092469599ad466b45e23a31
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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