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

HRID 1184900Notes

Reaction equation

HRID 1184900 reaction equation
[Cl:1][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>C1COCC1>[Cl:1][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

Participants

5

Reactant 3

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

Product 1

HCID 823939523-Chlorothieno[2,3-b]pyrazine-6-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-chlorothieno[2,3-b]pyrazine-6-carboxylate 92 (2.62 mmol, 600 mg) in 5 mL THF was added sodium hydroxide 2N in water (13.12 mmol, 6560 μl) and stirred at rt for 2 h. The reaction was quenched in 2N HCl extracted with CH2Cl2/methanol (9/1) (3×). Organic layers was dried and concentrated under reduced pressure to give 3-chlorothieno[2,3-b]pyrazine-6-carboxylic acid 93 (563 mg, 100%).

Workup

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

Sources & evidence

ORD record
ord-00c52eb6a4c04834841f83d62ad395a4
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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