2,2,2-Trifluoroethanol → HCID 89874843, compound

HRID 715427Notes

Reaction equation

HRID 715427 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:9]([O:11][CH3:12])=[O:10])=[N:6][C:7]=1[CH3:8].[F:13][C:14]([F:18])([F:17])[CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:8][C:7]1[N:6]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]=[N:3][C:2]=1[O:16][CH2:15][C:14]([F:18])([F:17])[F:13]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 12619146Methyl 5-chloro-6-methylpyrazine-2-carboxylate

Product 1

HCID 89874843HCID 89874843, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 5-chloro-6-methylpyrazine-2-carboxylate (3.00 g, 16.1 mmol), 2,2,2-trifluoroethanol (32.2 g, 322 mmol), and potassium carbonate (3.33 g, 24.1 mmol) in DMF (30 mL) is stirred at 60° C. for 2 hours. After cooling to rt, the mixture is filtered off, and the filtrate is diluted with EtOAc (300 mL). The organic layer is washed with water (100 mL×3) and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting EtOAc to give 3.91 g (97% yield) of the title compound as white solid.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe mixture is filtered off
  3. additionthe filtrate is diluted with EtOAc (300 mL)
  4. washThe organic layer is washed with water (100 mL×3)
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel
  9. washeluting EtOAc

Sources & evidence

ORD record
ord-73656ca36af74fd4bd130d921426ff79
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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