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

HRID 604066ノート

反応式

HRID 604066 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(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]+

後処理

  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)

出典と根拠

ORDレコード
ord-fbff05421c9143e287abd275c9a99589
出典データセット
uspto-grants-2011_03
特許番号
US07906517B2

反応ノート

読み込み中…