Ammonia → 2'-Deoxy-4'-C-ethynyl-2-fluoroadenosine
Reaction equation
C([O:4][C@@H:5]1[C@@:9]([C:15]#[CH:16])([CH2:10][O:11]C(=O)C)[O:8][C@@H:7]([N:17]2[C:26]3[N:25]=[C:24]([F:27])[N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[CH:18]2)[CH2:6]1)(=O)C.N>CO>[C:15]([C@:9]1([CH2:10][OH:11])[O:8][C@@H:7]([N:17]2[C:26]3[N:25]=[C:24]([F:27])[N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[CH:18]2)[CH2:6][C@@H:5]1[OH:4])#[CH:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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%).