Triethylamine → Benzyl (3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-carbamate

HRID 604204ノート

反応式

HRID 604204 の反応式
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)[CH2:6][NH:7][C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.C(N([CH2:29][CH3:30])CC)C.Cl[C:32](Cl)([O:34][C:35](=[O:41])OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)[CH2:6][N:7]([C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1)[C:35](=[O:41])[O:34][CH2:32][C:30]1[CH:29]=[CH:16][CH:17]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 57551007(3,5-Bis-trifluoromethyl-benzyl)-(5-bromopyrimidin-2-yl)-amine

生成物 1

HCID 86626518Benzyl (3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-carbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amine (10 g) and triethylamine (4.18 ml) are dissolved in methylene chloride (100 mL) and thereto is added triphosgene (2.97 g) under ice-cooling. The reaction solution is stirred at the same temperature for 30 minutes and concentrated under reduced pressure. The resulting residue is dissolved in tetrahydrofuran (100 mL) and thereto are added benzyl alcohol (3.88 ml) and triethylamine (10.45 ml) at room temperature and the mixture is stirred overnight. The reaction solution is diluted with ethyl acetate and washed with a saturated aqueous sodium bicarbonate solution and a 1N-hydrochloric acid. 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 benzyl (3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-carbamate (11.58 g). MS (m/z): 534/536 [M+H]+

後処理

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue is dissolved in tetrahydrofuran (100 mL)
  4. additionare added benzyl alcohol (3.88 ml) and triethylamine (10.45 ml) at room temperature
  5. stirringthe mixture is stirred overnight
  6. additionThe reaction solution is diluted with ethyl acetate
  7. washwashed with a saturated aqueous sodium bicarbonate solution
  8. washThe organic layer is washed with a saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. 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-71b7fc27ba8342e5bb6e3c5af96c8725
出典データセット
uspto-grants-2011_03
特許番号
US07906517B2

反応ノート

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