Dimethylformamide → 7-Benzyl-3-ethyl-3,7-dihydro-1H-purine-2,6-dione

HRID 323857Notes

Reaction equation

HRID 323857 reaction equation
[CH2:1]([N:3]1[C:11]2[N:10]=[CH:9][NH:8][C:7]=2[C:6](=[O:12])[NH:5][C:4]1=[O:13])[CH3:2].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[CH2:25]([N:8]1[C:7]2[C:6](=[O:12])[NH:5][C:4](=[O:13])[N:3]([CH2:1][CH3:2])[C:11]=2[N:10]=[CH:9]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 3507373-ethylxanthine

Product 1

HCID 220073037-Benzyl-3-ethyl-3,7-dihydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

180 g (1 mol) of 3-ethylxanthine were initially introduced into 1000 ml of dimethylformamide, the mixture was heated to 80° C. with stirring and, after the introduction of 88 g (0.64 mol) of potassium carbonate, treated dropwise with 133 g (1.05 mol) of benzyl chloride in the course of 1 hour. It was then stirred at 100° C. for 2 hours, treated with 1000 ml of water, and the precipitated product was filtered on a suction filter, washed with water until salt-free and dried in a vacuum drying oven at 100° C. If necessary, a further purification can be carried out by reprecipitating from 1 N sodium hydroxide solution using 4 N hydrochloric acid analogously to Example 1a).

Workup

  1. stirringIt was then stirred at 100° C. for 2 hours
  2. filtrationthe precipitated product was filtered on a suction
  3. filtrationfilter
  4. washwashed with water until salt-free and
  5. customdried in a vacuum
  6. customdrying oven at 100° C
  7. customIf necessary, a further purification
  8. customby reprecipitating from 1 N sodium hydroxide solution

Sources & evidence

ORD record
ord-2f1df5af9bd84380a8f67bba5825dc1a
Source dataset
uspto-grants-2001_04
Patent number
US06214992B1

Reaction notes

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