Water → 5-(Fluoromethoxy)pyrazine-2-carboxylic acid

HRID 1693169Notes

Reaction equation

HRID 1693169 reaction equation
C[Si](C)(C)[O-].[K+].[F:7][CH2:8][O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]([O:18]C)=[O:17])=[N:14][CH:15]=1.O.C(OCC)(=O)C>O1CCCC1>[F:7][CH2:8][O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]([OH:18])=[O:17])=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23668039Potassium trimethylsilanolateHCID 574756772-Pyrazinecarboxylic acid, 5-(fluoromethoxy)-, methyl ester

Product 1

HCID 574756765-(Fluoromethoxy)pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium trimethylsilanolate (18.6 mg) was added to a solution of methyl 5-fluoromethoxypyrazine-2-carboxylate obtained in Preparation Example 15-(1) (18.0 mg) in tetrahydrofuran (1.0 mL). The reaction solution was stirred at room temperature for one hour. Water and ethyl acetate were added to the reaction solution, and the aqueous layer was separated. The aqueous layer was made acidic with 1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a crude product of the title compound (10.2 mg). The compound was used for the next reaction without further purification.

Workup

  1. customthe aqueous layer was separated
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-703ebb2fec0241ee967e893338591caa
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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