(2-Benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]-amine → 2-({(3,5-Bis-trifluoromethyl-benzyl)-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]-amino}-methyl)-4-trifluoromethyl-phenol

HRID 604128Notes

Reaction equation

HRID 604128 reaction equation
C([O:8][C:9]1[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][C:10]=1[CH2:11][N:12]([CH2:26][C:27]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=1)[C:13]1[N:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:15][N:14]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[F:40][C:37]([F:38])([F:39])[C:29]1[CH:28]=[C:27]([CH:32]=[C:31]([C:33]([F:35])([F:34])[F:36])[CH:30]=1)[CH2:26][N:12]([CH2:11][C:10]1[CH:41]=[C:42]([C:45]([F:48])([F:47])[F:46])[CH:43]=[CH:44][C:9]=1[OH:8])[C:13]1[N:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:15][N:14]=1

Participants

4

Reactant 1

HCID 86626874(2-Benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]-amine

Product 1

HCID 866268752-({(3,5-Bis-trifluoromethyl-benzyl)-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]-amino}-methyl)-4-trifluoromethyl-phenolYield 42.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(2-Benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]-amine (1.07 g) is dissolved in ethanol (15 ml) and thereto is added 10% palladium-carbon (320 mg) and the mixture is stirred under hydrogen atmosphere at room temperature for 7 hours. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 2-({(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]-amino}-methyl)-4-trifluoromethyl-phenol (400 mg). MS (m/z): 618 [M+H]+

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-636090ea1451474fb638750bee216027
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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