Methyl iodide → HCID 54458499, compound

HRID 580895Notes

Reaction equation

HRID 580895 reaction equation
[CH3:1][O-].[Na+].[OH:4][CH2:5][CH2:6][C:7]1[C:8](=[O:15])[NH:9][C:10]([CH3:14])=[N:11][C:12]=1[CH3:13].IC>CO>[OH:4][CH2:5][CH2:6][C:7]1[C:8](=[O:15])[N:9]([CH3:1])[C:10]([CH3:14])=[N:11][C:12]=1[CH3:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 1354593675-(2-Hydroxyethyl)-2,6-dimethylpyrimidin-4-ol

Product 1

HCID 54458499HCID 54458499, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methylate (1.9 g) was added to a mixture of intermediate 4 (6 g) in methanol (50 ml) while stirring at RT. Stirring was continued for 30 minutes and iodomethane (5 g) was added dropwise and the reaction mixture was stirred and refluxed for 4 hours. The solvent was evaporated, water was added to the residue and this mixture was extracted with CH2Cl2. The organic layer was separated, dried over MgSO4, filtered and the solvent was evaporated, yielding 6.0 g (94%) of 5-(2-hydroxyethyl)-2,3,6-trimethyl-4(3H)-pyrimidinone (intermediate 5).

Workup

  1. stirringStirring
  2. stirringthe reaction mixture was stirred
  3. temperaturerefluxed for 4 hours
  4. customThe solvent was evaporated
  5. additionwater was added to the residue
  6. extractionthis mixture was extracted with CH2Cl2
  7. customThe organic layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-abee740f4edd41788d73bbb636a2ecbd
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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