2,2,2-Trifluoroethanol → HCID 68108403, compound

HRID 538381Notes

Reaction equation

HRID 538381 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:13][O:14][C:15]([C:17]1[C:22]([NH2:23])=[N:21][C:20](Cl)=[CH:19][N:18]=1)=[O:16].[NH4+].[Cl-]>>[CH3:13][O:14][C:15]([C:17]1[C:22]([NH2:23])=[N:21][C:20]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[CH:19][N:18]=1)=[O:16]

Participants

5

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 53417426Methyl 3-amino-5-chloropyrazine-2-carboxylate

Product 1

HCID 68108403HCID 68108403, compound

Procedure

A mixture of 2,2,2-trifluorethanol (6.9 ml, 96 mmol) and cesium carbonate (1.56 g, 4.8 mmol) was stirred for 20 min, 3-amino-5-chloro-pyrazine-2-carboxylic acid methyl ester (600 mg, 3.2 mmol; GB 1248146) was added and the mixture was stirred at rt for 42 h. To complete the reaction the mixture was heated to reflux for another 3 h. Saturated aq. NH4Cl was added and the mixture was extracted with EtOAc, the combined organic layers were washed with saturated aq. sodium chloride, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 3:7) to provide the title compound as colorless solid.

Workup

  1. stirringthe mixture was stirred at rt for 42 h
  2. customthe reaction the mixture
  3. temperaturewas heated
  4. temperatureto reflux for another 3 h
  5. extractionthe mixture was extracted with EtOAc
  6. washthe combined organic layers were washed with saturated aq. sodium chloride
  7. dry with materialdried with Na2SO4
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 3:7)

Sources & evidence

ORD record
ord-e7689de78b6f4040a1f8a9cb71db1851
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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