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

HRID 604080Notes

Reaction equation

HRID 604080 reaction equation
C([O:8][C:9]1[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][C:10]=1[CH2:11][N:12]([CH2:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=1)[C:13]1[N:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:15][N:14]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[F:39][C:36]([F:37])([F:38])[C:28]1[CH:27]=[C:26]([CH:31]=[C:30]([C:32]([F:33])([F:35])[F:34])[CH:29]=1)[CH2:25][N:12]([CH2:11][C:10]1[CH:40]=[C:41]([C:44]([F:47])([F:46])[F:45])[CH:42]=[CH:43][C:9]=1[OH:8])[C:13]1[N:18]=[CH:17][C:16]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[CH:15][N:14]=1

Participants

4

Reactant 1

HCID 86626833(2-Benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amine

Product 1

HCID 866268342-{[(3,5-Bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenolYield 71.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(2-Benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amine (2.46 g) is dissolved in ethanol (35 ml), and thereto is added 10% palladium-carbon (750 mg) and the mixture is stirred under hydrogen atmosphere at room temperature for 1 hour and 30 minutes. 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=4:1→3:2) to give 2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenol (1.53 g). MS (m/z): 581 [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=4:1→3:2)

Sources & evidence

ORD record
ord-5e0536a5b08f48aa921aacdfbc701b93
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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