Hexamethyldisilazane → HCID 178504300, compound

HRID 1452011Notes

Reaction equation

HRID 1452011 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 13838Hexamethyldisilazane2×HCID 6097028Ammonium SulfateHCID 178418229Cytosine

Product 1

HCID 178504300HCID 178504300, compound

Conditions

Temperature
120 °C

Procedure

Bis-trimethylsilylcytosine was prepared by combining 2.44 g of cytosine, 5.15 ml of hexamethyldisilazane and 580 mg of ammonium sulfate with 5 ml of xylenes and refluxing the solution at 120° C. for 1 hour. An additional 5 ml of hexamethyldisilazane were added to form a homogenous solution which was refluxed for 30 minutes. The xylenes and excess hexamethyldisilazane were removed and a gelatin-like bis-trimethylsilylcytosine formed. 5.6 g of the bis-trimethylsilylcytosine were reconstituted in 20 ml of xylenes. The xylenes were removed and the bis-trimethylsilylcytosine was again reconstituted in 20 ml of xylenes. The bis-trimethylsilylcytosine was evaporated to dryness and reconstituted in 5 ml of xylenes. 1 g of 2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoyl-1-α-methanesulfonate was reacted with the bis-trimethylsilylcytosine solution at 127° C. for 3.5 hours. HPLC analysis confirmed completion of the reaction.

Workup

  1. customBis-trimethylsilylcytosine was prepared
  2. customto form a homogenous solution which
  3. temperaturewas refluxed for 30 minutes
  4. customThe xylenes and excess hexamethyldisilazane were removed

Sources & evidence

ORD record
ord-8738f3ad0a554dc28d1fc3285f77d0ef
Source dataset
uspto-grants-1997_02
Patent number
US05606048

Reaction notes

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