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

HRID 1184931Notes

Reaction equation

HRID 1184931 reaction equation
Cl[C:2]1[N: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+].C1C[O:20][CH2:19][CH2:18]1>C(O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:19]([O:20][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[S:10][C:5]2=[N:4][CH:3]=1)[CH3:18]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86680165Methyl 2-chlorothieno[2,3-b]pyrazine-6-carboxylate

Product 1

HCID 671255822-Ethoxythieno[2,3-b]pyrazine-6-carboxylic acidYield 61%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-chlorothieno[3,2-b]pyrazine-6-carboxylate 22 (100 mg, 0.437 mmol) in THF (1.8 mL) and ethanol (1.2 mL) was added 2N sodium hydroxide (1.09 mL, 2.19 mmol). The reaction was stirred overnight at 50° C. The reaction mixture was poured in citric acid solution and the resulting precipitate was collected, washed with water and dried to give crude 2-ethoxythieno[2,3-b]pyrazine-6-carboxylic acid (60 mg, 61%). (m/z)=225 (M+H)+.

Workup

  1. customthe resulting precipitate was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-9edd452b5e164985b399193c5d342150
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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