Sodium hydride → 5-(benzyloxy)-2-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-3,4-dihydronaphthalene

HRID 1271295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271295
[H-].[Na+].[C:3]1([C:9]2[N:10]=[CH:11][C:12]([NH:21][CH3:22])=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:23]([O:30][C:31]1[CH:40]=[CH:39][CH:38]=[C:37]2[C:32]=1[CH2:33][CH2:34][C:35]([CH2:41]Cl)=[CH:36]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH2:23]([O:30][C:31]1[CH:40]=[CH:39][CH:38]=[C:37]2[C:32]=1[CH2:33][CH2:34][C:35]([CH2:41][N:21]([C:12]1[CH:11]=[N:10][C:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=1)[CH3:22])=[CH:36]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 12548150N-Methyl-5,6-diphenylpyrazin-2-amineHCID 229320295-(Benzyloxy)-2-(chloromethyl)-3,4-dihydronaphthalene

Produkt 1

HCID 184526575-(benzyloxy)-2-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-3,4-dihydronaphthaleneAusbeute 104,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under an argon atmospshere, 0.97 g of 60% sodium hydride was suspended in anhydrous N,N-dimethylformamide and 0.97 g of 5,6-diphenyl-2-(methylamino)-pyrazine was added in three portions. After stirring at 80° C. for 30 minutes, the reaction solution was ice-cooled and a solution of 0.97 g of 5-(benzyloxy)-2-(chloromethyl)-3,4-dihydronaphthalene in 5 ml of anhydrous N,N-dimethylformamide was added dropwise. After stirring for 30 minutes, the reaction solution was diluted with ice water and then extracted with diethyl ether. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.81 g of the desired compound as a pale yellow amorphous.

Aufarbeitung

  1. temperaturecooled
  2. stirringAfter stirring for 30 minutes
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7b023f3a3ff949f9a0f0f2fa3d5faf74
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205302B2

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