Methyl iodide → 2-Chloro-8-(methylsulfanyl)-7H-purine

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7](=[S:11])[NH:8]2)=[CH:4][N:3]=1.[OH-].[K+].I[CH3:15]>CCO>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([S:11][CH3:15])=[N:8]2)=[CH:4][N:3]=1

Participants

Procedure

To a stirring solution of 2-chloro-7H-purine-8(9H)-thione (2.00 g, 10.72 mmol) and potassium hydroxide (722 mg, 12.86 mmol) in anhydrous EtOH (66.4 mL) was added iodomethane (0.67 mL, 10.72 mmol). The reaction solution was stirred under N2 at RT for 4 h, then partitioned between EtOAc (85 mL) and 2N HCl (15 mL) and allowed to settle overnight. To the aqueous layer, which contained solid material, was added more water (60 mL). The mixture was filtered, and dried under vacuum to afford the title compound as a solid. LC-MS: calculated for C6H5ClN4S 199.99 observed m/e: 200.99 (M+H)+ (Rt 0.99/1.8 min).