Dimethyl Sulfate → HCID 178463891, compound

HRID 1579245Notes

Reaction equation

HRID 1579245 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 1N sodium hydroxide solution the pH value is kept between 7.5 and 8. A total of approximately 100 cc of 1N sodium hydroxide solution is additionally required. The mixture is stirred for a further 5 hours at room temperature and the precipitated crystals are filtered off at 5°; then they are washed with water. The crystalline product is subsequently triturated 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.

Workup

  1. temperaturecooled to 20°
  2. stirringThe mixture is stirred for a further 5 hours at room temperature
  3. filtrationthe precipitated crystals are filtered off at 5°
  4. washthen they are washed with water
  5. customThe crystalline product is subsequently triturated with 1500 cc of carbon tetrachloride by means of a vibration mixer
  6. filtrationfiltered
  7. concentrationthe carbon tetrachloride solution is then concentrated by evaporation, whereupon crystallization commences
  8. addition200 cc of petroleum ether are then added

Sources & evidence

ORD record
ord-4e2382571cd84b96800f6eaec83fb2e9
Source dataset
uspto-grants-1976_01
Patent number
US03931180

Reaction notes

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