2,4,6-Trimethylphenol → 7-benzyl-4-(2,4,6-trimethyl-phenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine

HRID 1516810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516810
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[H-].[Na+].[CH2:13]([N:20]1[C:24]2[N:25]=[C:26]([NH2:30])[N:27]=[C:28](Cl)[C:23]=2[CH:22]=[CH:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN1C=CC=CC1=O>[CH2:13]([N:20]1[C:24]2[N:25]=[C:26]([NH2:30])[N:27]=[C:28]([O:10][C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])[C:23]=2[CH:22]=[CH:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 105873407-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Produkt 1

HCID 576935647-benzyl-4-(2,4,6-trimethyl-phenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

To a solution of 2,4,6-trimethylphenol (161 mg, 1.16 mmol) in 1-methyl-2-pyridone (2 mL) in a sealed tube was added NaH (46 mg, 1.16 mmol). The reaction mixture was stirred at room temperature for 15 min and a solution of 7-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine (100 mg, 0.39 mmol) in 1-methyl-2-pyridone (1 mL) was added to the mixture. The mixture was heated at 150° C. for 16 h and cooled to room temperature. The reaction mixture was 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 107 mg (77%) of 7-benzyl-4-(2,4,6-trimethyl-phenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine.

Aufarbeitung

  1. temperatureThe mixture was heated at 150° C. for 16 h
  2. temperaturecooled to room temperature
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined organic solution was washed with H2O (20 mL) and brine (20 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-704c85b4bb6c440aa7fbe8dbbd52dbc2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227601B2

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