Hydrochloric Acid → 3-Amino-6-bromopyrazine-2-carboxylic acid

HRID 446908Notes

Reaction equation

HRID 446908 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=[O:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[Li+].[OH-].Cl>C1COCC1.O>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylate

Product 1

HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acidYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(Step 6-ii) To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (1 g, 4.33 mmol) in 10 mL THF was added a solution of LiOH (540 mg, 12.86 mmol) in 20 mL of water. The mixture was stirred at room temperature for 4 hours and acidified with 6M HCl to a pH of 2. The yellow precipitate was collected by filtration and washed with water. After drying in vacuo, the product, 3-amino-6-bromopyrazine-2-carboxylic acid (600 mg, 2.75 mmol, 64% yield), can be used directly in the next reaction without further purification.

Workup

  1. filtrationThe yellow precipitate was collected by filtration
  2. washwashed with water
  3. customAfter drying in vacuo

Sources & evidence

ORD record
ord-3ad9a43c816741c2b883b34a55125545
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Reaction notes

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