Sodium Hydroxide → 3-Amino-6-bromopyrazine-2-carboxylic acid

HRID 217770Notes

Reaction equation

HRID 217770 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]=1

Participants

4

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

  1. customMeOH was removed under a reduced pressure and water (300 mL)
  2. additionadded to the reaction mixture
  3. extractionThe solution was extracted with EtOAc
  4. washwashed with water
  5. extractionThe combined organic extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-1d8bc5e0eeab4aa7bd369bebd96bba48
Source dataset
uspto-grants-2012_06
Patent number
US08198285B2

Reaction notes

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