Dimethyl Sulfate → HCID 178463891, compound

HRID 442486Notes

Reaction equation

HRID 442486 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[N:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[N:5]=1)[CH3:2].S(OC)(O[CH3:18])(=O)=O>[OH-].[Na+]>[CH2:12]([N:3]([CH2:1][CH3:2])[C:4]1[N:5]=[C:6]([O:11][CH3:18])[CH:7]=[C:8]([OH:10])[N:9]=1)[CH3:13]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 178463892HCID 178463892, compound

Product 1

HCID 178463891HCID 178463891, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent3×

Procedure

500 cc of sodium hydroxide solution 1N are added while stirring to 91.5 g (0.5 mol) of 2-diethylamino-4,6-dihydroxy-pyrimidine. The solution is stirred at 50° for a short period and then cooled to 20°. 63 g (0.5 mol) of dimethyl sulphate are added dropwise, over the course of 1 hour, to the clear solution; by further addition of sodium hydroxide solution 1N the pH value is kept between 7.5 and 8. A total of approximately 100 cc of sodium hydroxide solution 1N is further used. The mixture is stirred for a further 5 hours at room temperature and filtered off at 5° from the precipitated crystals; then it is washed with water. The crystalline product is subsequently decomposed with 1500 cc of carbon tetrachloride by means of a vibration mixer. The undissolved parts are suction filtered and the carbon tetrachloride solution is then concentrated by evaporation, whereupon crystallization commences; 200 cc of petroleum ether are then added. The mixture is suction filtered, washed with petroleum ether and dried at 80° in a high vacuum. Optionally it may be recrystallized from benzene. M.P.: 165°-166°.

Workup

  1. temperaturecooled to 20°
  2. stirringThe mixture is stirred for a further 5 hours at room temperature
  3. filtrationfiltered off at 5° from the precipitated crystals
  4. washthen it is washed with water
  5. filtrationfiltered
  6. concentrationthe carbon tetrachloride solution is then concentrated by evaporation, whereupon crystallization commences
  7. addition200 cc of petroleum ether are then added
  8. filtrationfiltered
  9. washwashed with petroleum ether
  10. customdried at 80° in a high vacuum
  11. customOptionally it may be recrystallized from benzene

Sources & evidence

ORD record
ord-966af5ed696e4669b9ae70f4e828c8a8
Source dataset
uspto-grants-1977_08
Patent number
US04045561

Reaction notes

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