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

HRID 2112878Notes

Reaction equation

HRID 2112878 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

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

Workup

  1. additionwas added to the reaction solution
  2. filtrationthe white precipitate was collected by filtration
  3. customThe white solid obtained
  4. washwas washed with water and t-butyl methyl ether

Sources & evidence

ORD record
ord-59585e52edb3417ca746343ae27fb9c6
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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