4'-Mercaptoacetanilide → N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-phenylpyrimidin-2-ylthio)phenyl)acetamide

HRID 7612

Reaktionsgleichung

Reaktionsgleichung von HRID 7612
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:10][N:11]=[C:12]([CH3:14])[CH:13]=2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[C:21]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][CH:26]=1)(=[O:23])[CH3:22]>C(O)(C)(C)C>[C:21]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([S:31][C:2]2[N:7]=[C:6]([NH:8][C:9]3[NH:10][N:11]=[C:12]([CH3:14])[CH:13]=3)[CH:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=2)=[CH:27][CH:26]=1)(=[O:23])[CH3:22]

Komponenten

4

Edukt 2

HCID 707774'-MercaptoacetanilideHCID 178418761(2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine

Produkt 1

HCID 178419061N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-phenylpyrimidin-2-ylthio)phenyl)acetamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

The above prepared (2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine. (60 mg, 0.21 mmol) is combined with 4-acetamidothiophenol (176 mg, 1.05 mmol) in tert-butanol (5 mL) and the mixture heated at reflux for 20 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and aqueous NaHCO3. The organic layer is washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue is purified by flash chromatography (SiO2, DCM/MeOH gradient) to afford [2-(4-acetamido-phenylsulfanyl)-6-phenyl-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (74 mg, 85%)

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 20 hours
  3. custompartitioned between ethyl acetate and aqueous NaHCO3
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is purified by flash chromatography (SiO2, DCM/MeOH gradient)

Quellen und Nachweise

ORD-Eintrag
ord-2c9f0fe041d94e3aa4d71ea144b51227
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087603B2

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