Sodium hydride → 7-benzyl-4-(2,4,6-trimethyl-phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine

HRID 1805835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805835
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[SH: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>>[CH2:13]([N:20]1[C:24]2[N:25]=[C:26]([NH2:30])[N:27]=[C:28]([S: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

4

Edukt 3

HCID 24758Sodium hydrideHCID 2844492,4,6-TrimethylthiophenolHCID 105873407-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Produkt 1

HCID 576936297-benzyl-4-(2,4,6-trimethyl-phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamineAusbeute 94,2 %

Versuchsvorschrift

To a solution of 2,4,6-trimethylbenzene-1-thiol (231 mg, 1.52 mmol) in 1-methyl-2-pyrridone (2 mL) was added NaH (58 mg, 1.52 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 (131 mg, 0.51 mmol) in 1-methyl-2-pyrridone (2 mL) was added to the mixture. The mixture was heated at 60° C. for 16 h and cooled to room temperature. The reaction 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 180 mg (94%) of 7-benzyl-4-(2,4,6-trimethyl-phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine.

Aufarbeitung

  1. temperatureThe mixture was heated at 60° 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-128abe7da1bd4bdca85e9c39f152d9af
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354532B2

Notizen zur Reaktion

Wird geladen…