Methyl iodide → 5-(2-hydroxyethyl)-6-methyl-2-(methylsulfanyl)-4(3H)-pyrimidinone

HRID 847155Notes

Reaction equation

HRID 847155 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].[CH3:13][O-].[Na+].IC>CO>[OH:1][CH2:2][CH2:3][C:4]1[C:5](=[O:12])[NH:6][C:7]([S:11][CH3:13])=[N:8][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 1784335535-(2-hydroxyethyl)-6-methyl-2-sulfanyl-1H-pyrimidin-4-one

Product 1

HCID 1354111545-(2-hydroxyethyl)-6-methyl-2-(methylsulfanyl)-4(3H)-pyrimidinoneYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 90 parts of 5-(2-hydroxyethyl)-2-mercapto-6-methyl-4(3H)-pyrimidinone in 320 parts of methanol were added 90 parts of a sodium methoxide solution 30%. After stirring for 20 minutes, 72 parts of iodomethane were added and the whole was stirred and refluxed for 3 hours. The reaction mixture was evaporated in vacuo and water was added to the residue. The precipitated product was filtered off and crystallized from ethanol, yielding 78 parts (78%) of 5-(2-hydroxyethyl)-6-methyl-2-(methylthio)-4(3H)-pyrimidinone (interm. 1).

Workup

  1. stirringthe whole was stirred
  2. temperaturerefluxed for 3 hours
  3. customThe reaction mixture was evaporated in vacuo and water
  4. additionwas added to the residue
  5. filtrationThe precipitated product was filtered off
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-916701acee6c4b859a7c0eb630d48502
Source dataset
uspto-grants-1992_08
Patent number
US05140029

Reaction notes

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