Methyl iodide → 4-Methyl-2-(methylsulfanyl)pyrimidine

HRID 500704Notes

Reaction equation

HRID 500704 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([SH:8])[N:3]=1.IC.[C:11]([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178428686HCID 178428686, compound

Product 1

HCID 8212614-Methyl-2-(methylsulfanyl)pyrimidineYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of compound 4-methylpyrimidine-2-thiol (500 g, 3.05 mol), iodomethane (611 g, 4.27 mol) and K2CO3 (915 g, 6.71 mol) in THF (4 L) was stirred at room temperature for 18 h. The suspension was filtered and the solid was washed with ether (500 mL×2). The filtrate was concentrated and dried in vacuum to give compound 2 (380 g, 89.2%) as a yellow oil.

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with ether (500 mL×2)
  3. concentrationThe filtrate was concentrated
  4. customdried in vacuum

Sources & evidence

ORD record
ord-85c9c7bf7a0246fa9d3dd105ea2dd2f9
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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