Methyl iodide → 1-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)N-methylaminocarbonyl]-4-(2-methoxyphenyl)piperazine

HRID 1841462Notes

Reaction equation

HRID 1841462 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])[CH2:16][CH2:15]2)=[O:13])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8].[H-].[Na+].[CH3:30]I>CN(C)C=O>[CH3:1][C:2]1[N:3]=[C:4]([N:11]([CH3:30])[C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])[CH2:16][CH2:15]2)=[O:13])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 234461611-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazine

Product 1

HCID 99300251-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)N-methylaminocarbonyl]-4-(2-methoxyphenyl)piperazineYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[(5,6-Dimethyl-2-methoxypyrazin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazine (200 mg, 0.54 mmol) was dissolved in dimethylformamide (15 ml) and thereto 60% sodium hydride (21.5 mg, 0.54 mmol) was added. The resulting mixture was stirred at room temperature for 15 minutes, and thereto methyl iodide (76.6 mg, 0.54 mmol) was added. The resulting mixture was stirred at room temperature for 6 hours, concentrated under the reduced pressure to remove the solvent, and purified by column chromatography to obtain the titled compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 6 hours
  2. concentrationconcentrated under the reduced pressure
  3. customto remove the solvent
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-50377effd410407fa7698f37e0ed57a9
Source dataset
uspto-grants-2004_01
Patent number
US06683184B2

Reaction notes

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