Dimethylformamide → 8-Bromo-3-methyl-7-(3-methylbut-2-enyl)-1-(2-oxo-2-phenylethyl)-3,7-dihydropurine-2,6-dione

HRID 1360380Notes

Reaction equation

HRID 1360380 reaction equation
[Br:1][C:2]1[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:9]2[C:8](=[O:16])[NH:7][C:6](=[O:17])[N:5]([CH3:18])[C:4]=2[N:3]=1.[CH2:19](Br)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:9]2[C:8](=[O:16])[N:7]([CH2:19][C:20](=[O:21])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:6](=[O:17])[N:5]([CH3:18])[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 34353313-Methyl-7-(3-methyl-2-buten-1-yl)-8-bromo-xanthine

Product 1

HCID 247501618-Bromo-3-methyl-7-(3-methylbut-2-enyl)-1-(2-oxo-2-phenylethyl)-3,7-dihydropurine-2,6-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

30 g of 8-bromo-3-methyl-7-(3-methylbut-2-enyl)-3,7-dihydropurine-2,6-dione, 20.6 g of phenacyl bromide and 25.4 g of potassium carbonate are introduced into 400 ml of DMF and heated at an internal temperature of 80° C. for 3 hours. The solution is cooled to about 50° C., and 400 ml of water are slowly added. The mixture is then stirred overnight, and precipitated solid is filtered off with suction. After washing the water, the pale brown solid is recrystallized from 300 ml of isopropanol.

Workup

  1. temperatureThe solution is cooled to about 50° C.
  2. customprecipitated solid
  3. filtrationis filtered off with suction
  4. washAfter washing the water
  5. customthe pale brown solid is recrystallized from 300 ml of isopropanol

Sources & evidence

ORD record
ord-5e2c655aa8034e8da5fc300eda65f90c
Source dataset
uspto-grants-2011_02
Patent number
US07879864B2

Reaction notes

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