Reaction #1951040

Reaction equation

ammonia

Compound 3

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

→

2′-deoxy-4′-C-ethynyl-2-fluoroadenosine

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe resultant reaction mixture
2. 2
   Concentrationwas concentrated under reduced pressure
3. 3
   workup.ADDITIONa mixture of chloroform and methanol (20:1)
4. 4
   workup.ADDITIONwas added to the resultant residue
5. 5
   FiltrationThe thus-precipitated crystals were filtered
6. 6
   Otherthe resultant crystals were recrystallized from water

Procedure

Compound 3 (200 mg, 0.53 mmol) was dissolved in methanol (7.00 ml), and 28% aqueous ammonia (5.00 ml) was added to the resultant solution, followed by stirring at room temperature for four hours. The resultant reaction mixture was concentrated under reduced pressure, and a mixture of chloroform and methanol (20:1) was added to the resultant residue. The thus-precipitated crystals were filtered, and then the resultant crystals were recrystallized from water, to thereby yield compound 4 (113 mg, 0.39 mmol, 73.6%).

Source