Ammonium Hydroxide → 4'-Cyanothymidine
Reaction equation
[C:1]([C@:3]1([CH2:18][O:19]C(=O)C)[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17])#[N:2].[NH4+].[OH-]>CO>[C:1]([C@:3]1([CH2:18][OH:19])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17])#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4'-cyano-5'-O-acetylthymidine (0.85 g, 2.76 mM) and NH4OH (15 ml) in CH3OH (15 ml) was stirred at 24° C. for 2 hours. The solvent was removed by evaporation under pump vacuum. The residue was purified by flash chromatography on silica gel eluting with (7% CH3OH/CH2Cl2) and by preparative chromatography TLC affording 4'-cyanothymidine (300 mg, 1.12 mM). mp 238.5° C. to 242.5° C.