Diethyl Sulfate → HCID 23324656, compound

HRID 1380828Notes

Reaction equation

HRID 1380828 reaction equation
[Cl:1][CH2:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([OH:10])[CH:4]=1.S(OCC)(O[CH2:15][CH3:16])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:10][C:5]1[N:6]=[C:7]([CH3:9])[N:8]=[C:3]([CH2:2][Cl:1])[CH:4]=1)[CH3:16]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 178433451HCID 178433451, compound

Product 1

HCID 23324656HCID 23324656, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

15.8 g (0.1 mol) of 6-chloromethyl-4-hydroxy-2-methyl-pyrimidine, 13 ml (0.1 mol) of diethyl sulphate and 27.6 g (0.2 mol) of potassium carbonate are heated at reflux in 500 ml of acetone for 6 hours. The mixture is then filtered and the filtrate is concentrated to dryness. The residue is taken up in 200 ml of methylene chloride and the methylene chloride solution is washed once with 50 ml of 2N sodium hydroxide and twice with 50 ml of semi-saturated sodium chloride solution, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The residual oil is distilled at 47° C./0.07 mmHg, whereupon the distillate becomes solid. There is obtained 6-ethoxy-4-chloromethyl-2-methyl-pyrimidine, m.p. 29° C.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated to dryness
  3. washthe methylene chloride solution is washed once with 50 ml of 2N sodium hydroxide and twice with 50 ml of semi-saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated under reduced pressure
  6. distillationThe residual oil is distilled at 47° C./0.07 mmHg

Sources & evidence

ORD record
ord-86e51d68990f4b8b84e09f5a37e8864b
Source dataset
uspto-grants-1986_04
Patent number
US04584295

Reaction notes

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