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

HRID 882883Notes

Reaction equation

HRID 882883 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 the precipitated solid is filtered off with suction. After washing with water, the pale brown solid is recrystallized from 300 ml of isopropanol.

Workup

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

Sources & evidence

ORD record
ord-2f67497e5e3d4cb8b0963570cac38e6d
Source dataset
uspto-grants-2012_08
Patent number
US08236810B2

Reaction notes

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