Methyl iodide → 4,6-Dimethyl-2-(methylsulfanyl)pyrimidine

HRID 1729234Notes

Reaction equation

HRID 1729234 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([SH:15])[N:9]=1.[CH3:16]I>CC(C)=O>[CH3:16][S:15][C:10]1[N:11]=[C:12]([CH3:14])[CH:13]=[C:8]([CH3:7])[N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1784266324,6-dimethylpyrimidine-2-thiol

Product 1

HCID 123431744,6-Dimethyl-2-(methylsulfanyl)pyrimidineYield 82.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of potassium carbonate (27.6 g, 0.2 mol) in a solution of 4,6-dimethyl-2-mercaptopyrimidine (14 g, 0.1 mol) and methyl iodide (18.7 ml, 0.3 mol) in acetone (200 ml) was heated under reflux for 3 hours. The reaction mixture was allowed to cool before being filtered and then evaporated in vacuo. Distillation of the mixture at a pressure of 0.01 mmHg afforded 12.7 g 2-methylthio-4,6-dimethylpyrimidine as a white solid. A portion of this solid (4.42 g, 28.7 mmol) was dissolved in dichloromethane (200ml) and m-chloroperoxybenzoic acid (50%, 22.8 g, 66.0 mmol) was added in portions. The resulting mixture was stirred for a period of 5 days at the end of which it was first filtered and then evaporated in vacuo. Purification by flash column chromatography upon silica gel using diethyl ether as eluant afforded 3.35 g 2-methylsulphonyl-4,6-dimethylpyrimidine as a white solid, m.pt., 81° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. filtrationbefore being filtered
  5. customevaporated in vacuo
  6. distillationDistillation of the mixture at a pressure of 0.01 mmHg

Sources & evidence

ORD record
ord-c1c3744acc2b4b8eb0cd91f7ccdb5b85
Source dataset
uspto-grants-1994_07
Patent number
US05332745

Reaction notes

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