2,2,2-Trifluoroethanol → 5-Bromo-2-(2,2,2-trifluoroethoxy)pyrimidine

HRID 1678065Notes

Reaction equation

HRID 1678065 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.[CH2:12]([OH:17])[C:13]([F:16])([F:15])[F:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:17][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 3192865-Bromo-2-(methylsulphonyl)pyrimidine

Product 1

HCID 179595455-Bromo-2-(2,2,2-trifluoroethoxy)pyrimidineYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mechanically stirred slurry of 5-bromo-2-(methanesulfonyl)pyrimidine (24 g, 0.10 mol), trifluoroethanol (15 g, 0.15 mol), and potassium carbonate (28 g, 0.20 mol) in acetonitrile (250 mL) was heated at 70° C. for 12 hours. HPLC analysis indicated complete conversion. The solids were removed by filtration, and rinsed well with acetonitrile. The solvent was removed in vacuo and the residue partitioned between ether (50 mL) and water (25 mL). The aqueous phase was extracted with ether (2×25 mL), the organic layers combined, and washed with brine. Dried (Na2SO4), filtered, and solvent removed in vacuo, affording product as a pale yellow liquid, 19 g, 74 percent yield.

Workup

  1. customThe solids were removed by filtration
  2. washrinsed well with acetonitrile
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between ether (50 mL) and water (25 mL)
  5. extractionThe aqueous phase was extracted with ether (2×25 mL)
  6. washwashed with brine
  7. dry with materialDried (Na2SO4)
  8. filtrationfiltered
  9. customsolvent removed in vacuo
  10. customaffording product as a pale yellow liquid, 19 g, 74 percent yield

Sources & evidence

ORD record
ord-e22a2a4566a14d339027b0393de62c10
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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