Methyl iodide → HCID 19100928, compound

HRID 1085074Notes

Reaction equation

HRID 1085074 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([CH2:9][CH2:10][OH:11])=[C:4]([CH3:12])[N:3]=1.[CH3:13][O-].[Na+].IC>C(O)C>[NH2:1][C:2]1[N:7]([CH3:13])[C:6](=[O:8])[C:5]([CH2:9][CH2:10][OH:11])=[C:4]([CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 1354086952-Amino-5-(2-hydroxyethyl)-6-methylpyrimidin-4(1H)-one

Product 1

HCID 19100928HCID 19100928, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 67.7 parts of 2-amino-5-(2-hydroxyethyl)-6-methyl-4(3H)-pyrimidinone and 800 parts of ethanol were added 80 parts of a sodium methoxide solution 30%. The reaction mixture was heated to reflux temperature and 62.5 parts of iodomethane were added dropwise. Upon complete addition, stirring was continued for 4 hours at reflux temperature. The reaction mixture was evaporated and the residue was suspended in 400 parts of water. The precipitated product was filtered off, washed with 40 parts of ethanol and dried, yielding 58.3 parts (79.6%) of 2-amino-5-(2-hydroxyethyl)-3,6-dimethyl-4(3H)-pyrimidinone (interm. 10).

Workup

  1. temperatureThe reaction mixture was heated
  2. additionwere added dropwise
  3. additionUpon complete addition
  4. temperatureat reflux temperature
  5. customThe reaction mixture was evaporated
  6. filtrationThe precipitated product was filtered off
  7. washwashed with 40 parts of ethanol
  8. customdried

Sources & evidence

ORD record
ord-18326d76e478454d988421b17a0a144a
Source dataset
uspto-grants-1991_04
Patent number
US05008268

Reaction notes

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