CO[C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:11]=[N:12][C:13]([N:16]([CH3:18])C)=N[CH:15]=3)[S:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.[Cl-].[Cl-].[Ca+2].[C:28]([O-:31])(O)=O.[Na+].[CH2:33](Cl)Cl>>[CH3:28][O:31][C:20]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:33][C:13]([NH:16][CH3:18])=[N:12][CH:11]=3)=[N:7][C:6]=2[CH:19]=1To a stirred slurry of 5-(6-methoxy-1,3-benzothiazol-2-yl)-N,N-dimethylpyrimidin-2-amine (0.196 mg, 0.68 mmol) in DCM (2 mL) at 0° C. under argon, was added BBr3 (1 M in DCM, 4.1 mL) from a syringe. After 5 min of stirring, the reaction mixture was allowed to reach rt over 6.5 h, while being stirred under a drying tube (CaCl2). Then sat. aq. NaHCO3 was carefully added and the mixture was vigorously stirred at rt on before it was concentrated under vacuum. The residue was dissolved in MeOH, concentrated on and filtered through silica (EtOAc/MeOH 10:1). Purification by HPLC gave the title compound (12 mg) as yellow solid. 1H NMR δ 8.89 (s, 2H) 7.79 (d, 1H) 7.39 (d, 1H) 6.96 (dd, 1H) 3.22 (s, 6H); MS m/z (M+H) 273.
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