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

HRID 1524631Notes

Reaction equation

HRID 1524631 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.CCOC(C)=O>C1COCC1>[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 THF (1.0 mL). The reaction solution was stirred at RT for 1 h. Water and EtOAc 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 EtOAc. The organic layer was dried over anhydrous MgSO4. 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. 1H-NMR (400 MHz, CDCl3) δ (ppm): 6.16 (d, J=50.8 Hz, 2H), 8.34 (d, J=1.4 Hz, 1H), 9.05 (d, J=1.4 Hz, 1H).

Workup

  1. customthe aqueous layer was separated
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a45c6717cdd248e1b9814bfd1179e760
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

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