Hexamethyldisilazane → HCID 178504300, compound

HRID 1491946Notes

Reaction equation

HRID 1491946 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](N)=[N:4][C:2]1=[O:3].[CH3:9][Si:10]([CH3:17])([CH3:16])[NH:11][Si:12]([CH3:15])([CH3:14])[CH3:13].S([O-])([O-])(=O)=O.[NH4+].[NH4+]>>[CH3:9][Si:10]([N:11]([Si:12]([CH3:15])([CH3:14])[CH3:13])[C:8]1[CH:7]=[CH:5][NH:4][C:2](=[O:3])[N:1]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 13838HexamethyldisilazaneHCID 6097028Ammonium SulfateHCID 178418229Cytosine

Product 1

HCID 178504300HCID 178504300, compound

Procedure

Bis-trimethylsilylcytosine was prepared by combining 292 mg of cytosine with 2 ml of hexamethyldisilazane, 11 mg of ammonium sulfate and 5 ml of xylenes and refluxing the solution for one hour to form a homogenous solution. The excess xylenes and hexamethyldisilazane were removed leaving behind a molten residue of bis-trimethylsilylcytosine. 400 mg of 2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoyl-1-α-methanesulfonate, dissolved in 2 mi of xylenes, were added to the molten bis-trimethylsilylcytosine and the xylenes were removed. The temperature of the reaction mixture was maintained at 160° C. for 15 minutes. HPLC analysis confirmed completion of the reaction. The alpha to beta anomeric ratio of blocked nucleoside product was 1:1.3.

Workup

  1. customBis-trimethylsilylcytosine was prepared
  2. temperaturerefluxing the solution for one hour
  3. customto form a homogenous solution
  4. customThe excess xylenes and hexamethyldisilazane were removed

Sources & evidence

ORD record
ord-515fbec78f314d3f8873a705d8496b57
Source dataset
uspto-grants-1994_12
Patent number
US05371210

Reaction notes

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