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

HRID 646662Notes

Reaction equation

HRID 646662 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:18]Br>C(O)(=O)C.O>[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][C:5]([Br:18])=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24408Bromine2×HCID 72669Methyl 3-aminopyrazinecarboxylate2×

Product 1

HCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Commercially available methyl 3-amino-pyrazine-2-carboxylate (available from Aldrich Chemical Company) was brominated using a procedure similar to that of Russ, T., Ried, W., Ullrich, F., and Mutschler, E. Arch. Pharm. (Weinheim) 1992, 325, 761-767. To a solution of methyl 3-amino-2-pyrazine carboxylate (30.0 g, 200 mmol) in acetic acid (200 mL), bromine (11 mL) was added slowly via addition funnel. After complete addition of bromine, sodium carbonate powder was added slowly until precipitation occurred. The reaction mixture was allowed to stir at room temperature for 2 h. The reaction mixture was reduced to half-volume in vacuo and then diluted with water (500 mL). The reaction mixture was shaken vigorously and the resulting solid was collected using vacuum filtration. The solid was washed with ether to afford a pure yellow solid (91% yield).

Workup

  1. additionwas added slowly until precipitation
  2. stirringThe reaction mixture was shaken vigorously
  3. customthe resulting solid was collected
  4. filtrationvacuum filtration
  5. washThe solid was washed with ether

Sources & evidence

ORD record
ord-ad1be0b34c60482eb7d55180ee66c6de
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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