Acetic Acid → N-({2-[(cyclopentylmethyl)(ethyl)amino]-5-(trifluoromethyl)phenyl}methyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amine

HRID 1442514ノート

反応式

HRID 1442514 の反応式
[CH:1]1([CH2:6][N:7]([CH2:20][CH3:21])[C:8]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:9]=2[CH:10]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][S:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[N:29][C:30]([NH2:33])=[N:31][CH:32]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC=CC=1.O>[CH:1]1([CH2:6][N:7]([CH2:20][CH3:21])[C:8]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:9]=2[CH2:10][NH:33][C:30]2[N:29]=[CH:28][C:27]([O:26][CH2:25][CH2:24][S:23][CH3:22])=[CH:32][N:31]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 583396535-(2-(Methylthio)ethoxy)pyrimidin-2-amineHCID 866289762-[(Cyclopentylmethyl)(ethyl)amino]-5-(trifluoromethyl)benzaldehyde

生成物 1

HCID 68491507N-({2-[(cyclopentylmethyl)(ethyl)amino]-5-(trifluoromethyl)phenyl}methyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amine収率 84%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a solution of 2-[(cyclopentylmethyl)(ethyl)amino]-5-(trifluoromethyl)benzaldehyde (3.34 g, 11.2 mmol) obtained in Step 3 and 5-[2-(methylthio)ethoxy]pyrimidin-2-amine (2.27 g, 12.3 mmol) obtained in Step 1 in toluene (80 mL) was added acetic acid (317 mg, 5.19 mmol), and the mixture was refluxed by heating for 4 hours with a Dean-Stark apparatus. The reaction mixture was left to cool to room temperature, and then added with sodium triacetoxyborohydride (4.73 g, 22.3 mmol) on an ice bath with stirring, and the mixture was stirred at room temperature for 60 hours. The reaction mixture was added with water, and extracted with chloroform, and then the organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→10:1→4:1) to obtain N-({2-[(cyclopentylmethyl)(ethyl)amino]-5-(trifluoromethyl)phenyl}methyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amine (4.39 g, 84%) as a pale yellow oil.

後処理

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 4 hours with a Dean-Stark apparatus
  3. waitThe reaction mixture was left
  4. stirringthe mixture was stirred at room temperature for 60 hours
  5. extractionextracted with chloroform
  6. washthe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→10:1→4:1)

出典と根拠

ORDレコード
ord-c507afda087c41409dc7a9fa980c46be
出典データセット
uspto-grants-2010_02
特許番号
US07659271B2

反応ノート

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