Methanol → 4-Chloro-6-methoxy-2-(methylthio)pyrimidine

HRID 1449442Notes

Reaction equation

HRID 1449442 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH3:11][OH:12].[H-].[Na+].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:12][CH3:11])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 805314,6-Dichloro-2-(methylthio)pyrimidine

Product 1

HCID 98369994-Chloro-6-methoxy-2-(methylthio)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-dichloro-2-(methylthio)pyrimidine (Compound IV-5) (19.5 g, 0.100 mol) was dissolved in tetrahydrofuran (200 ml) just after distilled, then methyl alcohol (3.2 g, 0.100×1.0 mol) was added thereto. While cooling with ice, 60% sodium hydride (4.4 g, 0.100×1.1 mol) was added thereto while stirring. After stirred for 3 hours, the reaction solution was poured into water and extracted with toluene. The organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and filtered, and thereafter, the solvent was distilled off to obtain the compound (IV-29).

Workup

  1. distillationafter distilled
  2. additionwas added
  3. stirringAfter stirred for 3 hours
  4. extractionextracted with toluene
  5. washThe organic phase was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationthe solvent was distilled off
  9. customto obtain the compound (IV-29)

Sources & evidence

ORD record
ord-cadad98409cc438ebbfce371ac13aa94
Source dataset
uspto-grants-1997_02
Patent number
US05599770

Reaction notes

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