Potassium peroxymonosulphate → 2-chloro-8-(methylsulfonyl)-7H-purine

Reaktionsgleichung

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7](SC)=[N:8]2)=[CH:4][N:3]=1.[S:13]([O-:18])(O[O-])(=O)=[O:14].[K+].[K+].[CH3:21]C#N.O>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([S:13]([CH3:21])(=[O:18])=[O:14])=[N:8]2)=[CH:4][N:3]=1

Komponenten

Edukt 3

HCID 10313463Potassium peroxymonosulphate

HCID 18373917Acetonitrile--water (1/1)

HCID 457896422-Chloro-8-(methylsulfanyl)-7H-purine

Produkt 1

HCID 900418402-chloro-8-(methylsulfonyl)-7H-purine

Versuchsvorschrift

To a stirring solution of 2-chloro-8-(methylthio)-7H-purine (700.0 mg, 3.49 mmol) in 50% CH3CN/water (44.8 mL) was added potassium peroxymonosulfate (oxone, 4.72 g, 7.68 mmol). The reaction was stirred under N2 at RT for 17 h, then filtered and the filtrate was added to a stirring EtOAc (1 L)/water (0.56 L) mixture. The aqueous layer was separated and back-extracted with EtOAc (0.2 L). The combined organic layers were evaporated under reduced pressure to afford the title compound. LC-MS: calculated for C6H5ClN4O2S 231.98 observed m/e: 233.11 (M+H)+ (Rt 0.58/2.0 min).