Tert-butyl 4-{2-[(4-benzyloxy-5'-isopropyl-2'-methoxy-biphenyl-2-ylmethyl)-(3,5-bis-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yloxy}-butyrate → Tert-butyl 4-{2-[(3,5-bis-trifluoromethyl-benzyl)-(4-hydroxy-5'-isopropyl-2'-methoxy-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butyrate

HRID 604192Notes

Reaction equation

HRID 604192 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=2[O:24][CH3:25])=[C:11]([CH2:26][N:27]([CH2:45][C:46]2[CH:51]=[C:50]([C:52]([F:55])([F:54])[F:53])[CH:49]=[C:48]([C:56]([F:59])([F:58])[F:57])[CH:47]=2)[C:28]2[N:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[CH:30][N:29]=2)[CH:10]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[F:59][C:56]([F:57])([F:58])[C:48]1[CH:47]=[C:46]([CH:51]=[C:50]([C:52]([F:53])([F:54])[F:55])[CH:49]=1)[CH2:45][N:27]([CH2:26][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[C:15]1[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=1[O:24][CH3:25])[C:28]1[N:29]=[CH:30][C:31]([O:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])=[CH:32][N:33]=1

Participants

4

Reactant 1

HCID 86626920Tert-butyl 4-{2-[(4-benzyloxy-5'-isopropyl-2'-methoxy-biphenyl-2-ylmethyl)-(3,5-bis-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yloxy}-butyrate

Product 1

HCID 86626921Tert-butyl 4-{2-[(3,5-bis-trifluoromethyl-benzyl)-(4-hydroxy-5'-isopropyl-2'-methoxy-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butyrateYield 93.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Tert-butyl 4-{2-[(4-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-2-ylmethyl)-(3,5-bis-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yloxy}-butyrate (1.0 g) is dissolved in ethanol (20 ml), and thereto is added 10% palladium-carbon (200 mg), and the mixture is stirred under hydrogen atmosphere at room temperature for 4 hours. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure, and thereto is added hexane and the resulting crystal is filtered to give tert-butyl 4-{2-[(3,5-bis-trifluoromethyl-benzyl)-(4-hydroxy-5′-isopropyl-2′-methoxy-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butyrate (835 mg). MS (m/z): 734 [M+H]+

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. additionis added hexane
  4. filtrationthe resulting crystal is filtered

Sources & evidence

ORD record
ord-c05c215a4a4c40e9971012a39a37b26a
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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