Sodium Sulfate → Methyl 3-Amino-6-bromopyrazine-2-carboxylate

HRID 1817155Notes

Reaction equation

HRID 1817155 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:5]=[CH:4][N:3]=1.[Br:12]N1C(=O)CCC1=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[N:6][C:5]([Br:12])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 67184N-bromobutanimide2×HCID 72669Methyl 3-aminopyrazinecarboxylate

Product 1

HCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-aminopyrazine-3-carboxylate (5.0 g, 32.65 mmol) was dissolved in 100 mL of THF and treated with N-Bromosuccinimide (6.9 g, 39.18 mmol) all at once. The mixture was stirred at room temperature for 1.5 hrs, and then another 0.5 equivalents of N-bromosuccinimide was added and stirring continued for 1 hr. 10 grams of sodium sulfate were added, the mixture was vigorously stirred for 15 minutes, and the solvent was removed in vacuo. The residue obtained was suspended in 250 mL of water and stirred rapidly. Filtration afforded the title compound, methyl 3-amino-6-bromopyrazine-2-carboxylate, as a tan solid (6.33 g).

Workup

  1. stirringstirring
  2. waitcontinued for 1 hr
  3. stirringthe mixture was vigorously stirred for 15 minutes
  4. customthe solvent was removed in vacuo
  5. customThe residue obtained
  6. stirringstirred rapidly
  7. filtrationFiltration

Sources & evidence

ORD record
ord-68739d0f5bad49a280456bd06bf80286
Source dataset
uspto-grants-2009_10
Patent number
US07598251B2

Reaction notes

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