Ammonia → 9-(5-Deoxy-5,5-difluoropentofuranosyl)-9H-purin-6-amine

HRID 358790Notes

Reaction equation

HRID 358790 reaction equation
C([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:28]=2[N:29]=[CH:30][N:31]=1)[C@@H:15]1[O:27][C@H:23]([CH:24]([F:26])[F:25])[C@@H:18]([O:19]C(=O)C)[C@H:16]1[OH:17])(=O)C1C=CC=CC=1.N>C(O)C>[F:26][CH:24]([F:25])[C@H:23]1[O:27][C@@H:15]([N:14]2[C:28]3[N:29]=[CH:30][N:31]=[C:10]([NH2:9])[C:11]=3[N:12]=[CH:13]2)[C@H:16]([OH:17])[C@@H:18]1[OH:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86744653HCID 86744653, compound

Product 1

HCID 30831669-(5-Deoxy-5,5-difluoropentofuranosyl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 700 mg (1.5 mmol) of N6 -benzoyl-5'-deoxy-5',5'-difluoro-3'-O-acetyladenosine in 20 ml of ethanol in a Carius tube add gaseous ammonia while cooling in ice. Seal the tube and allow it to stand overnight. Open the tube and evaporate the solvent. Chromatograph the product on flash silica gel, (ethyl acetate/methanol) to give the title compound.

Workup

  1. temperaturewhile cooling in ice
  2. customSeal the tube
  3. customevaporate the solvent

Sources & evidence

ORD record
ord-82e74343885e41a78a04181d446dea9b
Source dataset
uspto-grants-1991_03
Patent number
US04997925

Reaction notes

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