Water → 3-Ethoxythieno[2,3-b]pyrazine-6-carboxylic acid

HRID 1184914Notes

Reaction equation

HRID 1184914 reaction equation
Cl[C:2]1[N:7]=[C:6]2[S:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1.[OH-].[Na+].O.C1C[O:21][CH2:20][CH2:19]1>CO>[CH2:20]([O:21][C:2]1[N:7]=[C:6]2[S:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1)[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86680178Methyl 3-chlorothieno[2,3-b]pyrazine-6-carboxylate

Product 1

HCID 671256133-Ethoxythieno[2,3-b]pyrazine-6-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-chlorothieno[2,3-b]pyrazine-6-carboxylate 92 (0.044 mmol, 10 mg) in methanol 250 uL and THF 250 uL was added sodium hydroxide 2N in water (0.219 mmol, 109 μA) and stirred overnight at rt. The reaction mixture was quenched in 2N HCl and extracted with CH2Cl2/methanol (9/1). The organic layer was dried and concentrated under reduced pressure to give 3-ethoxythieno[2,3-b]pyrazine-6-carboxylic acid 97 (9.3 mg, 100%).

Workup

  1. customThe reaction mixture was quenched in 2N HCl
  2. extractionextracted with CH2Cl2/methanol (9/1)
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57acba7d6d4b4dd6a83c3f0e9bd0900d
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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