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

HRID 2376715Notes

Reaction equation

HRID 2376715 reaction equation
[OH-].[Na+].Cl.[CH3:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([SH:11])[N:6]=1.I[CH3:13]>O>[CH3:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([S:11][CH3:13])[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 1784286872-Mercapto-4-methylpyrimidine hydrochloride

Product 1

HCID 8212614-Methyl-2-(methylsulfanyl)pyrimidineYield 86.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of NaOH (7.46 g, 186.4 mmol) in water (120 mL), 4-methylpyrimidine-2-thiol hydrochloride (13.78 g, 84.7 mmol) was added and subsequently iodomethane (13.23 g, 93.2 mmol) was added dropwise under argon atmosphere. It was stirred at room temperature for 2 h. It was extracted with CH2Cl2 (×2). The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 10.26 g of the desired compound (yield: 86%).

Workup

  1. extractionIt was extracted with CH2Cl2 (×2)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe crude product obtained
  5. customwas purified by chromatography on silica gel
  6. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-1ee8adbd7982446cb348b2ee663e3f24
Source dataset
uspto-grants-2008_12
Patent number
US07468376B2

Reaction notes

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