(2'-Benzyloxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(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-biphenyl-2-ol

HRID 604115Notes

Reaction equation

HRID 604115 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[CH2:25][N:26]([CH2:39][C:40]1[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[C:42]([C:50]([F:53])([F:52])[F:51])[CH:41]=1)[C:27]1[N:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[CH:29][N:28]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[F:53][C:50]([F:51])([F:52])[C:42]1[CH:41]=[C:40]([CH:45]=[C:44]([C:46]([F:47])([F:49])[F:48])[CH:43]=1)[CH2:39][N:26]([CH2:25][C:16]1[CH:17]=[C:18]([C:21]([F:22])([F:23])[F:24])[CH:19]=[CH:20][C:15]=1[C:10]1[C:9]([OH:8])=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:27]1[N:32]=[CH:31][C:30]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)=[CH:29][N:28]=1

Participants

4

Reactant 1

HCID 86626864(2'-Benzyloxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amine

Product 1

HCID 866268652'-{[(3,5-Bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4'-trifluoromethyl-biphenyl-2-olYield 70.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(2′-Benzyloxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amine (606 mg) is dissolved in ethanol (10 ml), and thereto is added 10% palladium-carbon (100 mg) and the mixture is stirred under hydrogen atmosphere at room temperature for 3.5 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=9:1→7:3) to give 2′-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4′-trifluoromethyl-biphenyl-2-ol (374 mg). MS (m/z): 657 [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=9:1→7:3)

Sources & evidence

ORD record
ord-27a2c9abe24b40008f252f6b2afeb2c6
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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