Reaction #1951041

Reaction equation

ammonia

Compound 7

3′,5′-di-O-acetyl-4′-C-cyano-2′-deoxy-2-fluoroadenosine

→

4′-C-cyano-2′-deoxy-2-fluoroadenosine

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe resultant reaction mixture
2. 2
   Concentrationwas concentrated under reduced pressure
3. 3
   Otherthe resultant residue was purified by means of silica gel column chromatography (silica gel 10 ml, hexane/ethyl acetate (5:1), ethyl acetate, ethyl acetate/methanol (10:1))

Procedure

Compound 7 (53.7 mg, 0.142 mmol) was dissolved in methanol (1.90 ml), and 28% aqueous ammonia (1.30 ml) was added to the resultant solution, followed by stirring at room temperature for 30 minutes. The resultant reaction mixture was concentrated under reduced pressure, and then the resultant residue was purified by means of silica gel column chromatography (silica gel 10 ml, hexane/ethyl acetate (5:1), ethyl acetate, ethyl acetate/methanol (10:1)), to thereby yield compound 8 (30.2 mg, 0.10 mmol, 72.3%).

Source