Methyl iodide → 6-Hydroxy-1-methyl-2-(methylsulfanyl)pyrimidin-4(1h)-one

HRID 440219Notes

Reaction equation

HRID 440219 reaction equation
[Na].[CH3:2][NH:3][C:4]([NH2:6])=[S:5].[C:7]([O:14]C)(=O)[CH2:8][C:9](OC)=[O:10].[CH3:16]I>CO>[OH:14][C:7]1[N:6]=[C:4]([S:5][CH3:16])[N:3]([CH3:2])[C:9](=[O:10])[CH:8]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7943Dimethyl malonateHCID 2723704MethylthioureaHCID 5360545Sodium

Product 1

HCID 1354085986-Hydroxy-1-methyl-2-(methylsulfanyl)pyrimidin-4(1h)-oneYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

In 250 ml of methanol was dissolved 13.1 g of metal sodium. To the resulting methanol solution were added 25 g (0.28 mol) of N-methylthiourea and 38.5 g (0.29 mol) of dimethyl malonate, and the mixture was reacted under reflux for 3 hours. Thereafter, to the solution was added dropwise 41.3 g (0.29 mol) of methyl iodide at 10° C. or lower, and the mixture was reacted at room temperature overnight. After completion of the reaction, methanol was removed under reduced pressure, and then the residue was dissolved in water. The resulting aqueous solution was made acidic with hydrochloric acid, and crystals precipitated were filtered, washed with water and dried to obtain 42.4 g (yield: 89%) of 6-hydroxy-3-methyl-2-methylthio-4(3H)-pyrimidinone.

Workup

  1. customthe mixture was reacted
  2. temperatureunder reflux for 3 hours
  3. customlower, and the mixture was reacted at room temperature overnight
  4. customwas removed under reduced pressure
  5. dissolutionthe residue was dissolved in water
  6. customprecipitated
  7. filtrationwere filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-20cbe130bf3c4c9c99fb05d56cdcf748
Source dataset
uspto-grants-1996_05
Patent number
US05518994

Reaction notes

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