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

HRID 1442514노트

반응식

HRID 1442514 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c507afda087c41409dc7a9fa980c46be
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659271B2

반응 노트

불러오는 중…