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

HRID 1296699Notes

Reaction equation

HRID 1296699 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([SH:8])[N:3]=1.[OH-].[Na+].I[CH3:12]>>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178428686HCID 178428686, compound

Product 1

HCID 8212614-Methyl-2-(methylsulfanyl)pyrimidineYield 98%

Procedure

4-Methylpyrimidine-2-thiol (79.4 g. 488 mmol) was added to 1M aqueous sodium hydroxide (NaOH) (1.02 L, 1.02 mol). To the stirring mixture was added iodomethane (76.2 g, 540 mmol) and the reaction-stirred at room temperature overnight. The mixture was extracted with dichloromethane (3×300 mL). The organic phase was dried over magnesium sulfate and concentrated to yield 66.8 g (98%) of 4-methyl-2-(methylsulfanyl)pyrimidine. 1H NMR (CDCl3): δ 8.39 (d, 1H), 6.84 (d, 1H), 2.59 (s, 3H), 2.48 (s, 3H); MS m/z 141 (M+1).

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×300 mL)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9128a1d124dd41dbb0530b3a33fcec26
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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