Imidazole → HCID 18670406, compound

HRID 1059395Notes

Reaction equation

HRID 1059395 reaction equation
[N:1]1[C:9]([CH:10]([OH:12])[CH3:11])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C)C=O>[O:12]([CH:10]([C:9]1[N:1]=[CH:2][N:3]=[C:4]2[C:8]=1[NH:7][CH:6]=[N:5]2)[CH3:11])[Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18670461HCID 18670461, compound

Product 1

HCID 18670406HCID 18670406, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.543 g of 1-(purin-6-yl)ethanol in N,N-dimethylformamide (10 ml) were added 0.27 g of imidazole and 0.598 g of tert-butyldimethylsilyl chloride and the resulting mixture was stirred at room temperature for 15 hours. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.793 g of the title compound as a white solid.

Workup

  1. distillationAfter distilling off the solvent under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-509496cd838244658f49c50406b3142e
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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