Sodium Methoxide → 2-(ethylthio)-5-(2-hydroxyethyl)-6-methyl-4(3H)-pyrimidinone

HRID 580892Notes

Reaction equation

HRID 580892 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5](=[O:12])[NH:6][C:7]([SH:11])=[N:8][C:9]=1[CH3:10].C[O-].[Na+].[I-].[CH3:17][CH3:18]>CO>[CH2:17]([S:11][C:7]1[NH:6][C:5](=[O:12])[C:4]([CH2:3][CH2:2][OH:1])=[C:9]([CH3:10])[N:8]=1)[CH3:18]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 18513229Ethane;iodideHCID 1784335535-(2-hydroxyethyl)-6-methyl-2-sulfanyl-1H-pyrimidin-4-one

Product 1

HCID 1361744192-(ethylthio)-5-(2-hydroxyethyl)-6-methyl-4(3H)-pyrimidinoneYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of intermediate 1 (37.2 g) and sodium methylate (36 g) in methanol (250 ml) was stirred for 30 min. Ethane iodide (31.2 g) was added dropwise. The reaction mixture was stirred and refluxed for 3 hours. The solvent was evaporated and the residue was stirred in water, filtered and recrystallized from CH3CN. The precipitate was filtered off and dried, yielding 26 g (60%) of 2-(ethylthio)-5-(2-hydroxyethyl)-6-methyl-4(3H)-pyrimidinone (intermediate 2).

Workup

  1. stirringThe reaction mixture was stirred
  2. temperaturerefluxed for 3 hours
  3. customThe solvent was evaporated
  4. stirringthe residue was stirred in water
  5. filtrationfiltered
  6. customrecrystallized from CH3CN
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-58e320e6469e409fb1f4545ce0580a3b
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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