Water → 2-bromo-N-(5-methylpyrazin-2-yl)acetamide

HRID 2192316Notes

Reaction equation

HRID 2192316 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:15][CH2:16][C:17](Br)=[O:18].O>CN(C=O)C>[Br:15][CH2:16][C:17]([NH:8][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][N:6]=1)=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 61147Bromoacetyl bromideHCID 3132155-Methylpyrazin-2-amine

Product 1

HCID 593162612-bromo-N-(5-methylpyrazin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-methyl-pyrazin-2-ylamine and cesium carbonate (11.2 g) dissolved in dry DMF (30 mL) was added by dropwise addition bromoacetylbromide (2.89 g) and the mixture stirred at rt for 2 hours. Water (200 mL) was added and the mixture extracted with ethyl acetate (2×100 mL) and dried over magnesium sulfate. Concentration of the extract to ˜50 mL and addition of isohexane (100 mL) gave the sub-titled compound as a solid (1.64 g).

Workup

  1. extractionthe mixture extracted with ethyl acetate (2×100 mL)
  2. dry with materialdried over magnesium sulfate
  3. extractionConcentration of the extract to ˜50 mL and addition of isohexane (100 mL)

Sources & evidence

ORD record
ord-054691063b1a44ea94dfbd91cf400a74
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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