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

HRID 1453578

Reaction equation

HRID 1453578 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+].Cl[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 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 6228DimethylformamideSolvent

Procedure

945 mg of 2,6-dichloropurine, 15 ml of DMF (dimethylformamide) and 288 mg of NaH are mixed and left at ambient temperature for 2 hours. 1.06 ml of 2-chloromethoxyethyltrimethylsilane are then added. The mixture is stirred for 18 hours at ambient temperature. The DMF is evaporated off. The product is taken up in methylene chloride. Washing is carried out with a saturated sodium bicarbonate solution and then once with H2O and, finally, with a saturated NaCl solution. Drying over Na2SO4 and evaporation to dryness are carried out. Purification is carried out by chromatography on silica with a CHCl3-AcOEt: 5-5 mixture for eluent. 876 mg of expected product are obtained, in the form of a yellow-colored oil.

Workup

  1. customThe DMF is evaporated off
  2. washWashing
  3. dry with materialDrying over Na2SO4 and evaporation to dryness
  4. customPurification

Sources & evidence

ORD record
ord-9dae688878cc4cd98e06386b3760b190
Source dataset
uspto-grants-2009_01
Patent number
US07476670B2

Linked notes

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