Methyl iodide → 5-Methyl-2-(methylthio)pyrimidin-4(3H)-one

HRID 1514405Notes

Reaction equation

HRID 1514405 reaction equation
[OH-].[K+].[CH3:3][C:4]1[C:5](=[O:11])[NH:6][C:7](=[S:10])[NH:8][CH:9]=1.[CH3:12]I>CCO>[CH3:3][C:4]1[C:5](=[O:11])[NH:6][C:7]([S:10][CH3:12])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 7204712-Thiothymine

Product 1

HCID 2405755-Methyl-2-(methylthio)pyrimidin-4(3H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 85% KOH (3.3 g, 50.7 mmol) and 5-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (7.2 g, 50.7 mmol) in absolute EtOH (100 ml) was stirred for 1 hour and then MeI (7.2 g, 50.7 mmol) was added dropwise. After refluxing the mixture for 2 hours, the solvent was removed under vacuum. The residue was triturated with water and the solid was filtered and dried in an oven to give 6.86 g of the title compound as a white powder (87% yield).

Workup

  1. temperatureAfter refluxing the mixture for 2 hours
  2. customthe solvent was removed under vacuum
  3. customThe residue was triturated with water
  4. filtrationthe solid was filtered
  5. customdried in an oven

Sources & evidence

ORD record
ord-339f389248c345f3b5ca1005760d6832
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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