Sodium Hydroxide → 2-Oxo-1,2-dihydrothieno[3,2-b]pyrazine-6-carboxylic acid

HRID 1184892Notes

Reaction equation

HRID 1184892 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:11]([O:13]C)=[O:12])[S:10][C:5]=2[N:4]=[CH:3]1.[OH-].[Na+]>CO>[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[S:10][C:5]=2[N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67125557Methyl 2-oxo-1,2-dihydrothieno[2,3-b]pyrazine-6-carboxylate

Product 1

HCID 671255862-Oxo-1,2-dihydrothieno[3,2-b]pyrazine-6-carboxylic acidYield 57.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-oxo-1,2-dihydrothieno[3,2-b]pyrazine-6-carboxylate 21 (50 mg, 0.238 mmol) in methanol (3 mL) was added a solution of 2N sodium hydroxide (0.238 mL, 0.476 mmol). The reaction was stirred at rt for 2 h. Quenched with 2N HCl solution and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated to give crude 2-oxo-1,2-dihydrothieno[3,2-b]pyrazine-6-carboxylic acid 84 (27 mg, 57%).

Workup

  1. customQuenched with 2N HCl solution
  2. extractionextracted with EtOAc
  3. washOrganic layer was washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-5223ab19b26b4888b3501df6d5745985
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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