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

HRID 1958946Notes

Reaction equation

HRID 1958946 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.FC1C(F)=CC=CC=1CSC1N=C(NS(N2CCC2)(=O)=O)C=[C:31]([O:43]C(CO)CO)N=1.[H-].[Na+].O>CO>[Cl:1][C:2]1[CH:7]=[C:6]([O:43][CH3:31])[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

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11698344N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamideHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of Example 1, step (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-b193a4d6ec174357b8888c9e8eaf1730
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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