Sodium Hydroxide → 3-Amino-6-bromopyrazine-2-carboxylic acid
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.[OH-].[Na+]>CO>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of the product of step (iii) (200 g, 0.86 mol) in MeOH (500 mL) was added 5 N—NaOH (500 mL) slowly. The resulting mixture was stirred at 50° C. for 3 hours. MeOH was removed under a reduced pressure and water (300 mL) added to the reaction mixture. The solution was acidified to pH 3 with 6N—HCl. The solution was extracted with EtOAc and washed with water. The combined organic extract was dried over Na2SO4, filtered and evaporated to dryness to afford the subtitle compound (iv) as a brown yellow solid (180 g).
Workup
- customMeOH was removed under a reduced pressure and water (300 mL)
- additionadded to the reaction mixture
- extractionThe solution was extracted with EtOAc
- washwashed with water
- extractionThe combined organic extract
- dry with materialwas dried over Na2SO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-1d8bc5e0eeab4aa7bd369bebd96bba48
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198285B2
Reaction notes
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