Adenine → HCID 19910051, compound

HRID 1452012Notes

Reaction equation

HRID 1452012 reaction equation
[N:1]1[C:9](N)=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+].[CH3:18][Si:19]([CH3:26])([CH3:25])[NH:20][Si:21]([CH3:24])([CH3:23])[CH3:22]>>[CH3:18][Si:19]([N:20]([Si:21]([CH3:24])([CH3:23])[CH3:22])[C:9]1[N:1]=[CH:2][N:3]=[C:4]2[C:8]=1[NH:7][CH:6]=[N:5]2)([CH3:26])[CH3:25]

Participants

4

Reactant 3

HCID 190AdenineHCID 13838HexamethyldisilazaneHCID 6097028Ammonium Sulfate

Product 1

HCID 19910051HCID 19910051, compound

Procedure

Bis-trimethylsilyladenine was prepared by combining 7 g of adenine and 109 ml of hexamethyldisilazane with 250 mg of ammonium sulfate and heating the mixture at 110°-115° C. for 8 hours. The solution was refluxed for an additional 30 minutes and the excess hexamethyldisilazane subsequently removed and 14.5 g of the bis-trimethylsilyladenine were reconstituted in 3 ml of anisole. 1.58 g of 2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoyl-1-α-methanesulfonate were reacted with the bis-trimethylsilyladenine solution at 105° C.-110° C. for 24 hours. HPLC analysis confirmed completion of the reaction.

Workup

  1. temperatureheating the mixture at 110°-115° C. for 8 hours
  2. temperatureThe solution was refluxed for an additional 30 minutes
  3. customthe excess hexamethyldisilazane subsequently removed
  4. custom1.58 g of 2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoyl-1-α-methanesulfonate were reacted with the bis-trimethylsilyladenine solution at 105° C.-110° C. for 24 hours
  5. customcompletion of the reaction

Sources & evidence

ORD record
ord-1cdd0e22b6c241c3a7ae5289f62b5d67
Source dataset
uspto-grants-1997_02
Patent number
US05606048

Reaction notes

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