Cesium carbonate → 6-(Difluoromethoxy)-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinol

HRID 2388741Notes

Reaction equation

HRID 2388741 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([OH:18])[N:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Na+].Cl[C:27]([F:32])([F:31])C([O-])=O>CN(C=O)C.O>[F:31][CH:27]([F:32])[O:18][C:13]1[N:12]=[C:11]([S:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[N:16]=[C:15]([OH:17])[CH:14]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 178516654HCID 178516654, compound

Product 1

HCID 1785166036-(Difluoromethoxy)-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-[[(2,3-difluorophenyl)methyl]thio]-4,6-pyrimidinediol (3 g) in DMF (30 mL), cesium carbonate (4.3 g) and chlorodifluoro-acetic acid sodium salt (1.9 g) was added. The resulting mixture was heated at 100° C. for 2 h. The reaction mixture was cooled then diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O and dried (MgSO4), filtered and evaporated. Purification was by column chromatography on silica gel using EtOAc/isohexane (2:8) as eluent to give the subtitle compound as a white solid. Yield: 0.4 g

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification

Sources & evidence

ORD record
ord-d892a5331f12482ea8c7accd8240e893
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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