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

HRID 646766Notes

Reaction equation

HRID 646766 reaction equation
C[O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([Br:12])[N:6]=1)=[O:4].[OH-].[Li+].Cl>C1COCC1.O>[NH2:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([Br:12])=[CH:8][N:9]=1

Participants

5

Reactant 3

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

Product 1

HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl-3-amino-6-bromopyrazine carboxylate (10 g, 43 mmol) in THF:H2O (3:1), lithium hydroxide (6.0 g, 140 mmol) was added. The reaction mixture was stirred at room temperature and monitored by LCMS. The reaction was complete after 1 h. The reaction mixture was poured into 1 N HCl (250 mL), extracted with ethyl acetate (3×, 200 mL), washed with brine (3×, 100 mL), dried over anhydrous sodium sulfate, filtered and concentrated to afford a yellow solid (100% yield).

Workup

  1. extractionextracted with ethyl acetate (3×, 200 mL)
  2. washwashed with brine (3×, 100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ef17635b49e34061a2cef3a790bcd071
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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