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

HRID 1951202Notes

Reaction equation

HRID 1951202 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([SH:9])[N:3]=1.[OH-].[Na+].[CH3:12]I>C(O)C.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:12])[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 1784266324,6-dimethylpyrimidine-2-thiol

Product 1

HCID 123431744,6-Dimethyl-2-(methylsulfanyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4,6-Dimethyl-pyrimidine-2-thiol (20 g, 142 mmol) is added slowly to a solution of sodium hydroxide (6.3 g, 156 mmol) in ethanol (120 ml) and water (60 ml). Methyl iodide (9.8 ml, 156 mmol) is added dropwise and the mixture is stirred at room temperature for 1 hour. The solvents are removed in vacuo and the residue is partitioned between diethyl ether (200 ml) and water (200 ml). The organic extract is dried (MgSO4) and the solvent is removed to give the titled compound.

Workup

  1. customThe solvents are removed in vacuo
  2. customthe residue is partitioned between diethyl ether (200 ml) and water (200 ml)
  3. extractionThe organic extract
  4. dry with materialis dried (MgSO4)
  5. customthe solvent is removed

Sources & evidence

ORD record
ord-f41d75e86fa94ae8b84769669dce56d5
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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