2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → (2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate

HRID 897108Notes

Reaction equation

HRID 897108 reaction equation
[Cu][C:2]#[N:3].[C:4]([O:7][C@H:8]1[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20](Cl)=[N:21][C:22]=3[Cl:26])[O:10][C@@H:9]1[CH2:28][O:29][C:30](=[O:32])[CH3:31])(=[O:6])[CH3:5]>O>[C:4]([O:7][C@H:8]1[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([C:2]#[N:3])=[N:21][C:22]=3[Cl:26])[O:10][C@@H:9]1[CH2:28][O:29][C:30](=[O:32])[CH3:31])(=[O:6])[CH3:5]

Participants

4

Reactant 2

HCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 178418546HCID 178418546, compound

Product 1

HCID 22948625(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Copper (I) cyanide was added to a solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate (J. Med. Chem., 248, 35, 1992) (22 g, 40 mmol) in N′N′-dimethylformamide (150 ml). The suspension was heated to 100° C. for 2 hours and was then allowed to cool to room temperature. The reaction mixture was poured into water (700 ml) with stirring. The solid was filtered off and stirred in dichloromethane (700 ml) for 30 minutes. The solid was filtered off again and then stirred in dichloromethane (700 ml) for another 30 minutes. The dichloromethane portions were combined and evaporated under reduced pressure to a volume of 500 ml. The dichloromethane was then dried over anhydrous sodium sulphate. The solvent was removed under reduced presure. The residue was redissolved in dichloromethane (300 ml). The solvent was removed under reduced pressure. The residue was then stirred in diethylether (300 ml) for 20 minutes. The solid was filtered off and dried to give the title compound (14.8 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe solid was filtered off
  3. stirringstirred in dichloromethane (700 ml) for 30 minutes
  4. filtrationThe solid was filtered off again
  5. stirringstirred in dichloromethane (700 ml) for another 30 minutes
  6. customevaporated under reduced pressure to a volume of 500 ml
  7. dry with materialThe dichloromethane was then dried over anhydrous sodium sulphate
  8. customThe solvent was removed
  9. dissolutionThe residue was redissolved in dichloromethane (300 ml)
  10. customThe solvent was removed under reduced pressure
  11. stirringThe residue was then stirred in diethylether (300 ml) for 20 minutes
  12. filtrationThe solid was filtered off
  13. customdried

Sources & evidence

ORD record
ord-2332e19eb8904861bc0c71c06d584c88
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

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