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

HRID 1271295Notes

Reaction equation

HRID 1271295 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 184526575-(benzyloxy)-2-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-3,4-dihydronaphthaleneYield 104.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7b023f3a3ff949f9a0f0f2fa3d5faf74
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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