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

HRID 1184830Notes

Reaction equation

HRID 1184830 reaction equation
[Cl:1][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+]>C1COCC1.C(O)C.Cl>[Cl:1][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

Participants

6

Reactant 2

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

Product 1

HCID 866801662-Chlorothieno[2,3-b]pyrazine-6-carboxylic acidYield 89%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-chlorothieno[3,2-b]pyrazine-6-carboxylate 22 (1.23 g, 5.38 mmol) in THF (10 mL) and ethanol (10 mL) was added a solution of 2N sodium hydroxide (13.45 mL, 26.9 mmol). The reaction was stirred at rt for 1 h. The reaction mixture was poured in 2N HCl solution and the resulting precipitate was collected, washed with water and dried to give crude 2-chlorothieno[3,2-b]pyrazine-6-carboxylic acid 23 (1.027 g, 89%). NMR (400 MHz, DMSO-d6) 8.18 (s, 1H), 8.90 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-167a8d32dbdc4723a01e563dcb68ac35
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

Loading…