Methanol → 4-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine

HRID 1175395Notes

Reaction equation

HRID 1175395 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.[H-].[Na+].[OH2:21].[CH3:22]O>>[Cl:1][C:2]1[CH:7]=[C:6]([O:21][CH3:22])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Product 1

HCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine

Procedure

To a stirred solution of 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of Example 1, step ii) (5 g) in dry methanol (40 mL) was added 60% sodium hydride (0.68 g) batchwise over 5 min. The reaction mixture was stirred for 5 h, H2O added and the solvents were partially evaporated. The residue was extracted with EtOAc which was washed with H2O, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with Et2O/iso-hexane (5:95) to give the subtitle compound as a white solid. Yield: 4.05 g.

Workup

  1. customthe solvents were partially evaporated
  2. extractionThe residue was extracted with EtOAc which
  3. washwas washed with H2O
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with Et2O/iso-hexane (5:95)

Sources & evidence

ORD record
ord-fde739aaac2a498fa3aa2fee3d599c42
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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