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

HRID 1442514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442514
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c507afda087c41409dc7a9fa980c46be
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659271B2

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