Sodium hydride → 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]butyloxy}acetic Acid Methyl Ester

HRID 1271288Notes

Reaction equation

HRID 1271288 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([NH:19][CH3:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:23][O:24][C:25](=[O:33])[CH2:26][O:27][CH2:28][CH2:29][CH2:30][CH2:31]Br>CN(C)C=O>[CH3:23][O:24][C:25](=[O:33])[CH2:26][O:27][CH2:28][CH2:29][CH2:30][CH2:31][N:19]([C:10]1[CH:9]=[N:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:11]=1)[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12548150N-Methyl-5,6-diphenylpyrazin-2-amineHCID 858402522-(4-Bromobutyloxy)acetic acid methyl ester

Product 1

HCID 693554312-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]butyloxy}acetic Acid Methyl EsterYield 20.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, to a solution of 763 mg of 5,6-diphenyl-2-(methylamino)pyrazine in 4 ml of N,N-dimethylformamide, 140 mg of 60% sodium hydride was added, followed by stirring at 80° C. for 30 minutes. The reaction solution was ice-cooled and a solution of 657 mg of 2-(4-bromobutyloxy)acetic acid methyl ester in 2 ml of N,N-dimethylformamide was slowly added. After an ice bath was removed, the mixture was stirred at room temperature for 14 hours. The reaction solution was combined with ice water and extracted with ethyl acetate and, after the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 240 mg of the desired compound as a pale yellow oily substance.

Workup

  1. temperaturecooled
  2. customAfter an ice bath was removed
  3. stirringthe mixture was stirred at room temperature for 14 hours
  4. extractionextracted with ethyl acetate
  5. washafter the extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a971f42d66a04bb4a6394f50bb0de966
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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