[Br:1][C:2]1[C:3]([NH:18][CH:19]([CH3:21])[CH3:20])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[N-:22]=[N+]=[N-].[Na+].S(=O)(=O)(O)O.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([NH:18][CH:19]([CH3:21])[CH3:20])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([CH3:17])(=[NH:22])=[O:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1185 mg (0.50 mmol) of (RS)-5-bromo-N4-isopropyl-N2-[4-(methyl sulfinyl)phenyl]-pyrimidine-2,4-diamine in 1 ml of DCM is mixed with 40 mg (0.55 mmol) of sodium azide. The batch is slowly mixed with 0.13 ml of concentrated sulfuric acid at 0° C. and then heated to 45° C. After 16 hours, the batch is cooled to room temperature, mixed with 2 ml of 1N NaOH solution and extracted from ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (DCM/EtOH 9:1). 38 mg (0.10 mmol, corresponding to 20% of theory) of the product is obtained.
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