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

HRID 501364Notes

Reaction equation

HRID 501364 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

112 g of 7-(2-butynyl)-3-methyl-3,7-dihydropurine-2,6-dione was dissolved in 2200 ml of N,N-dimethylformamide, and 75.3 g of N-chlorosuccinimide was added thereto. The resulting mixture was stirred at room temperature for five hours. 2200 ml of water was added to the reaction solution, and the mixture was stirred at room temperature for 1.5 hour. The white precipitate was collected by filtration, and the white solid was washed with water and, with t-butyl methyl ether. Thus, 117 g of the title compound was obtained.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hour
  2. filtrationThe white precipitate was collected by filtration
  3. washthe white solid was washed with water and, with t-butyl methyl ether

Sources & evidence

ORD record
ord-0dcea47bc73c4b889355dfa66d070d9d
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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