Benzyl Alcohol → (2-Benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amine

HRID 604066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604066
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([C:20]1[N:25]=[CH:24][C:23]([Br:26])=[CH:22][N:21]=1)[CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1F.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[H-].[Na+].O>O1CCCC1.C(OCC)(=O)C>[CH2:36]([O:43][C:10]1[CH:11]=[CH:12][C:13]([C:15]([F:18])([F:16])[F:17])=[CH:14][C:9]=1[CH2:8][N:7]([CH2:6][C:5]1[CH:27]=[C:28]([C:30]([F:32])([F:31])[F:33])[CH:29]=[C:3]([C:2]([F:1])([F:34])[F:35])[CH:4]=1)[C:20]1[N:21]=[CH:22][C:23]([Br:26])=[CH:24][N:25]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

7

Edukt 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 86626777(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-(2-fluoro-5-trifluoromethyl-benzyl)-amine

Produkt 1

HCID 86626822(2-Benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-(2-fluoro-5-trifluoromethyl-benzyl)-amine (11.1 g) is dissolved in tetrahydrofuran (20 ml), and thereto are added benzyl alcohol (6 ml) and sodium hydride (60%) (2.32 g), and the mixture is heated under reflux overnight. 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=97:3→9:1) to give (2-benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amine (12.9 g). MS (m/z): 664/666 [M+H]+

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  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=97:3→9:1)

Quellen und Nachweise

ORD-Eintrag
ord-fbff05421c9143e287abd275c9a99589
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

Notizen zur Reaktion

Wird geladen…