Dimethylformamide → 2,6-Dichloro-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purine

HRID 2238649Notes

Reaction equation

HRID 2238649 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[H-].[Na+].CN(C)C=O.[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24]Cl>O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:27])([CH3:26])[CH3:19])=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 53244122,6-Dichloropurine

Product 1

HCID 582852322,6-Dichloro-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 g of 2,6-dichloropurine was added to the mixture of 1.54 g of sodium hydride and 100 mL of N,N-dimethylformamide in an ice bath, and stirred at the same temperature for 15 minutes. 6.81 mL of 2-(trimethylsilyl)ethoxymethyl chloride was added to the reaction mixture, and was stirred at the same temperature for 5 hours. The reaction mixture was added with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine in the subsequent order, and then dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then purified by silica gel column chromatography, to obtain 6.18 g of 2,6-dichloro-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purine [56-1] as a light brown oily product.

Workup

  1. stirringwas stirred at the same temperature for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine in the subsequent order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-f1d2066a20f64014a5990180a35a4a01
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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