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Sodium hydride → 2,3-Dimethyl-8-(2,6-dimethylbenzyloxy)imidazo[1,2-a]pyrazine

HRID 1058571
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1058571
[H-].[Na+].[CH3:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=1[CH2:6][OH:7].Cl[C:14]1[C:15]2[N:16]([C:20]([CH3:24])=[C:21]([CH3:23])[N:22]=2)[CH:17]=[CH:18][N:19]=1>C(#N)C>[CH3:23][C:21]1[N:22]=[C:15]2[C:14]([O:7][CH2:6][C:5]3[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:4]=3[CH3:3])=[N:19][CH:18]=[CH:17][N:16]2[C:20]=1[CH3:24]
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 186748(2,6-Dimethylphenyl)methanolHCID 107499238-Chloro-2,3-dimethylimidazo[1,2-a]pyrazine

Produkt 1

HCID 99038552,3-Dimethyl-8-(2,6-dimethylbenzyloxy)imidazo[1,2-a]pyrazineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Sodium hydride (0.15 g, 3 mmol) (50% in oil) was added to a stirred solution of 2,6-dimethylbenzylalcohol in acetonitril (10 ml). 8-chloro-2,3-dimethylimidazo[1,2-a]pyrazine (0.4 g, 3 mmol) was added and the reaction mixture was refluxed for 20 h. The solvent was evaporated under reduced pressure and the residue was solved in methylene chloride and washed with water. The organic layer was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using ethylacetate:petroleum ether(40-60) 1:1 as eluent. Crystallization from petroleum ether gave 0.42 g (50%) of the title compound.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. washwashed with water
  4. customThe organic layer was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel
  6. customCrystallization from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-6dadd8d37f48432a8dc1e428596493c5
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06518270B1

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