4-Aminobenzonitrile → 4-[7-benzyl-4-(2,4,6-trimethyl-phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-benzonitrile

HRID 1516814

Reaktionsgleichung

Reaktionsgleichung von HRID 1516814
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:12]([N:19]1[C:23]2[N:24]=[C:25](F)[N:26]=[C:27]([S:28][C:29]3[C:34]([CH3:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=3[CH3:37])[C:22]=2[CH:21]=[CH:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN1C=CC=CC1=O>[CH2:12]([N:19]1[C:23]2[N:24]=[C:25]([NH:1][C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)[N:26]=[C:27]([S:28][C:29]3[C:30]([CH3:37])=[CH:31][C:32]([CH3:36])=[CH:33][C:34]=3[CH3:35])[C:22]=2[CH:21]=[CH:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 133964-AminobenzonitrileHCID 24758Sodium hydrideHCID 576936087-benzyl-2-fluoro-4-(2,4,6-trimethyl-phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 576935704-[7-benzyl-4-(2,4,6-trimethyl-phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-benzonitrileAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 127551-Methyl-2(1H)-pyridinoneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-aminobenzonitrile (184 mg, 1.56 mmol) in 1-methyl-2-pyridone (2 mL) was added NaH (62 mg, 1.56 mmol). The reaction mixture was stirred at room temperature for 15 min and a solution of 7-benzyl-2-fluoro-4-(2,4,6-trimethyl-phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine (118 mg, 0.31 mmol) in 1-methyl-2-pyridone (2 mL) was added to the mixture. The mixture was stirred at room temperature for 4 h, then poured into ice water and extracted with EtOAc (2×20 mL). The combined organic solution was washed with H2O (20 mL) and brine (20 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (Hexanes:EtOAc=75:25) yielded 123 mg (83%) of 4-[7-benzyl-4-(2,4,6-trimethyl-phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-benzonitrile.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 4 h
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic solution was washed with H2O (20 mL) and brine (20 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-15fde36e44e04387bdf4f375aaacdde7
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227601B2

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