Dimethyl Sulfate → HCID 178493578, compound

HRID 1395145Notes

Reaction equation

HRID 1395145 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[CH:8]1([C:11]2[N:16]=[C:15](O)[CH:14]=[C:13]([OH:18])[N:12]=2)[CH2:10][CH2:9]1>[OH-].[Na+]>[CH:8]1([C:11]2[N:12]=[C:13]([OH:18])[CH:14]=[C:15]([O:6][CH3:7])[N:16]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 178516636HCID 178516636, compound

Product 1

HCID 178493578HCID 178493578, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
50 °C

Procedure

76 g (0.6 mol) of dimethyl sulphate were added dropwise to a solution of 76 g (0.5 mol) of 2-cyclopropyl-4,6-dihydroxy-pyrimidine in 250 ml of 2 N sodium hydroxide solution at 50° C. The pH value of the reaction solution was kept at 8 to 8.2 by simultaneously adding 2 N sodium hydroxide solution. The mixture was then stirred at 50° C. for a further 2 hours, control of the pH being continued. The mixture was then cooled to 0° C. and the product which had precipitated was filtered off. 33 g (40% of theory) of 2-cyclopropyl-4-hydroxy-6-methoxy-pyrimidine were obtained in this manner in the form of colorless crystals with a melting point of 186° C.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. customthe product which had precipitated
  3. filtrationwas filtered off

Sources & evidence

ORD record
ord-d2d3e75a31af42b3ab6b56e269693f29
Source dataset
uspto-grants-1980_05
Patent number
US04202889

Reaction notes

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