Dimethylformamide → 7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-Purine-2,6-dione

HRID 501363Notes

Reaction equation

HRID 501363 reaction equation
Br[CH2:2][C:3]#[C:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[CH3:12][N:13]1[C:21]2[N:20]=[CH:19][NH:18][C:17]=2[C:16](=[O:22])[NH:15][C:14]1=[O:23].CN(C)C=O>O>[CH2:2]([N:18]1[C:17]2[C:16](=[O:22])[NH:15][C:14](=[O:23])[N:13]([CH3:12])[C:21]=2[N:20]=[CH:19]1)[C:3]#[C:4][CH3:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 706393-MethylxanthineHCID 27568621-Bromo-2-butyne

Product 1

HCID 220293647-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-Purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

55.3 ml of 1-bromo-2-butyne and 84.9 g of anhydrous potassium carbonate were added to a mixture of 100 g of 3-methyl xanthine [CAS No. 1076-22-8] and 1000 ml of N,N-dimethylformamide. The resulting mixture was stirred at room temperature for 18 hours. 1000 ml of water was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. The resulting white precipitate was collected by filtration. The white solid was washed with water and then t-butyl methyl ether. Thus, 112 g of the title compound was obtained.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. filtrationThe resulting white precipitate was collected by filtration
  3. washThe white solid was washed with water

Sources & evidence

ORD record
ord-a326bf09d1a64b7fae40d6de358d8c5c
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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