FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:14]=[CH:13][N:12]=[C:11]2[N:15]([CH:19]([C:21]3[C:22]([O:40][CH3:41])=[C:23]([CH:29]4[CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30]4)[C:24]([CH3:28])=[C:25]([Cl:27])[CH:26]=3)[CH3:20])[N:16]=[C:17]([Br:18])[C:10]=12>C(Cl)Cl.[OH-].[Na+]>[NH:31]1[CH2:32][CH:29]([C:23]2[C:22]([O:40][CH3:41])=[C:21]([CH:19]([N:15]3[C:11]4=[N:12][CH:13]=[N:14][C:9]([NH2:8])=[C:10]4[C:17]([Br:18])=[N:16]3)[CH3:20])[CH:26]=[C:25]([Cl:27])[C:24]=2[CH3:28])[CH2:30]1Trifluoroacetic acid (1.2 mL, 16 mmol) was added to a solution of tert-butyl 3-{3-[1-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}azetidine-1-carboxylate (224 mg, 0.407 mmol) in methylene chloride (2.5 mL) and stirred for 2 h at room temp. The mixture was diluted with dichloromethane and 1 N NaOH was added and stirred rapidly for a few minutes. The layers were separated and the aqueous extracted with dichloromethane. The combined organics were dried (MgSO4), filtered, and concentrated. Drying in vacuo gave 163 mg (91%) of the freebase. LCMS calculated for C18H21BrClN6O (M+H)+: m/z=451.1; Found: 451.0.
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