Ethyl Acetate → (3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amine

HRID 603994ノート

反応式

HRID 603994 の反応式
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[N:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:20][CH3:21].[Br:35][C:36]1[CH:37]=[N:38][C:39](Cl)=[N:40][CH:41]=1.C(NC(C(C)C)(C(C)C)C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[F:1][C:2]([F:33])([F:34])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][N:7]([C:39]1[N:40]=[CH:41][C:36]([Br:35])=[CH:37][N:38]=1)[CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[CH:12]=[CH:11][C:10]=1[N:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:20][CH3:21]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 6066655-Bromo-2-chloropyrimidineHCID 21936557DiisopropyldiethylamineHCID 86626753{2-[(3,5-Bis-trifluoromethyl-benzylamino)-methyl]-4-trifluoromethyl-phenyl}-butyl-ethyl-amine

生成物 1

HCID 86626754(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amine収率 86.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

{2-[(3,5-Bis-trifluoromethyl-benzylamino)-methyl]-4-trifluoromethyl-phenyl}-butyl-ethyl-amine (4.6 g), 5-bromo-2-chloropyrimidine (3.56 g) and N-ethyldiisopropylethylamine (4.8 ml) are dissolved in toluene (100 ml) and the mixture is heated under reflux overnight. The reaction solution is cooled to room temperature, and thereto are added ethyl acetate and water, 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=19:1→9:1) to give (3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amine (5.24 g). MS (m/z): 657/659 [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=19:1→9:1)

出典と根拠

ORDレコード
ord-30c70d9c10894479ad0083c082b2ba03
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…