Water → 7-(But-2-YN-1-YL)-8-chloro-3-methyl-3,7-dihydro-1H-purine-2,6-dione

HRID 2112879Notes

Reaction equation

HRID 2112879 reaction equation
[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[NH:11][C:10](=[O:15])[N:9]([CH3:16])[C:8]=2[N:7]=[CH:6]1)[C:2]#[C:3][CH3:4].[Cl:17]N1C(=O)CCC1=O.O>CN(C)C=O>[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[NH:11][C:10](=[O:15])[N:9]([CH3:16])[C:8]=2[N:7]=[C:6]1[Cl:17])[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 220293647-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-Purine-2,6-dione

Product 1

HCID 220298307-(But-2-YN-1-YL)-8-chloro-3-methyl-3,7-dihydro-1H-purine-2,6-dioneYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(2-Butynyl)-3-methyl-3,7-dihydropurine-2,6-dione (112 g) was dissolved in N,N-dimethylformamide (2200 mL), then N-chlorosuccinimide (75.3 g) was added to this mixture, and the reaction solution was stirred at room temperature for five hours. After completion of the reaction, water (2200 mL) was added to the reaction solution, this was stirred at room temperature for 1.5 hours. A white precipitate was then collected by filtration. The white solid obtained was washed with water and t-butyl methyl ether to give the title compound (117 g).

Workup

  1. additionwas added to the reaction solution
  2. stirringthis was stirred at room temperature for 1.5 hours
  3. filtrationA white precipitate was then collected by filtration
  4. customThe white solid obtained
  5. washwas washed with water and t-butyl methyl ether

Sources & evidence

ORD record
ord-c053b270f8dd477fa62b1a72d559da35
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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