Sodium Carbonate → 3-Amino-6-bromopyrazine-2-carboxamide

HRID 646733Notes

Reaction equation

HRID 646733 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[Br:11]Br.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][C:5]([Br:11])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 280292Aminopyrazine carboxamide

Product 1

HCID 4708993-Amino-6-bromopyrazine-2-carboxamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution 3-aminopyrazine-2-carboxamide (3 g, 22 mmol) in acetic acid (25 mL) was drop wise added bromine (4.2 g, 26.5 mmol) at room temperature the reaction mixture was stirred for 0.5 h and Na2CO3 (2 eq) was added slowly. Upon added of the reaction, the solvent was removed in vacuo, water (50 mL) was added to the residue and the precipitate was collected on a filter and washed with hexane (50 mL) to give 3-amino-6-bromopyrazine-2-carboxamide (4.5 g) as a yellow solid: MS (EI) for C5H5BrN4O: 217 (MH+).

Workup

  1. customat room temperature
  2. additionUpon added of the reaction
  3. customthe solvent was removed in vacuo, water (50 mL)
  4. additionwas added to the residue
  5. customthe precipitate was collected on
  6. filtrationa filter
  7. washwashed with hexane (50 mL)

Sources & evidence

ORD record
ord-0f32a80fd4ef4fb69a00664f568ed0fe
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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