Potassium Hydroxide → 7-Aminothieno[2,3-b]pyrazine-6-carboxylic acid

HRID 1184818Notes

Reaction equation

HRID 1184818 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([O:13]CC)=[O:12].[OH-].[K+]>C1COCC1.C(O)C.O>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 2820821Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate

Product 1

HCID 122257127-Aminothieno[2,3-b]pyrazine-6-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (10 g, 44.8 mmol) and potassium hydroxide (5.0 g, 90 mmol) in THF (50 mL), ethanol (50 mL) and water (20 mL) was stirred at 70° C. for 2 h. Quenched in a cold solution of 2N HCl, and the resulting precipitate was collected to give crude 7-aminothieno[2,3-b]pyrazine-6-carboxylic acid 8 (8.59 g, 98%). 1H-NMR (400 MHz, DMSO-d6) 7.03 (br s, 2H), 8.77 (s, 2H), 12.8 (br s, 1H).

Workup

  1. customQuenched in a cold solution of 2N HCl
  2. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-f270f6023dde41efb34cc1b5a38acce1
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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