4-Chloro-2-methylthiopyrimidine → 4-Ethoxy-2-(methylsulfanyl)pyrimidine

HRID 914408Notes

Reaction equation

HRID 914408 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[O-:10][CH2:11][CH3:12].[Na+]>C(O)C>[CH2:11]([O:10][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1)[CH3:12]

Participants

4

Reactant 2

HCID 971134-Chloro-2-methylthiopyrimidineHCID 2723922Sodium ethoxide

Product 1

HCID 2781014-Ethoxy-2-(methylsulfanyl)pyrimidineYield 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-2-(methylthio)pyrimidine (3.0 g) was dissolved in ethanol (30 mL), sodium ethoxide (2.54 g) was added, and the mixture was stirred at 60° C. for 10 hr. The reaction mixture was cooled, and the solvent was concentrated under reduced pressure. Water was added, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (3.0 g) as a slightly yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionWater was added
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3989c979b91544b78c60ec5ed8ec308c
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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