Dimethyl Sulfate → HCID 178493585, compound

HRID 442488Notes

Reaction equation

HRID 442488 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[C:5]([OH:10])[N:4]=1.[OH-].[Na+].S(OC)(O[CH3:17])(=O)=O>CCOCC.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:17])[CH:6]=[C:5]([OH:10])[N:4]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 178494256HCID 178494256, compound

Product 1

HCID 178493585HCID 178493585, compound

Reagents, catalysts & solvents 1

HCID 21911965Chloroform etherSolvent

Procedure

142 g (1 mol) of 2-methoxy-4,6-dihydroxypyrimidine are added while stirring to 500 cc of sodium hydroxide solution 2N and the mixture is stirred at 50° for 1 hour. Subsequently it is cooled to room temperature and 139 g (1.1 mol) of dimethyl sulphate are added dropwise while stirring; by the addition of sodium hydroxide solution 2N the pH value is kept at between 8.0 and 8.2. The mixture is stirred at 50° for a further 2 hours, cooled to room temperature and extracted with chloroform. After drying the chloroform phase over sodium sulphate the solvent is decanted in a vacuum. A white powder is obtained. After decomposition with ether/chloroform (1:1), the substance has a M.P. of 197°-201°.

Workup

  1. stirringwhile stirring
  2. stirringThe mixture is stirred at 50° for a further 2 hours
  3. temperaturecooled to room temperature
  4. extractionextracted with chloroform
  5. dry with materialAfter drying the chloroform phase over sodium sulphate the solvent
  6. customis decanted in a vacuum
  7. customA white powder is obtained

Sources & evidence

ORD record
ord-1f73a67fb4c44b94b5d8ab9f807d7cd4
Source dataset
uspto-grants-1977_08
Patent number
US04045561

Reaction notes

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