[CH3:1][O:2][C:3](=[O:38])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:20]4[CH2:29][CH2:28][C:23]5(OCC[O:24]5)[CH2:22][CH2:21]4)[N:18]=[CH:19][C:14]3=[C:13]([N:30]3[CH2:36][CH:35]4[O:37][CH:32]([CH2:33][CH2:34]4)[CH2:31]3)[N:12]=2)=[CH:7][CH:6]=1>Cl>[CH3:1][O:2][C:3](=[O:38])[NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:20]4[CH2:29][CH2:28][C:23](=[O:24])[CH2:22][CH2:21]4)[N:18]=[CH:19][C:14]3=[C:13]([N:30]3[CH2:36][CH:35]4[O:37][CH:32]([CH2:33][CH2:34]4)[CH2:31]3)[N:12]=2)=[CH:9][CH:10]=1Methyl{4-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate (0.2 g, 0.38 mmol) was dissolved in conc. HCl (2.0 mL) and stirred at room temperature for 1 hr. The reaction was cooled in an ice bath and basified with 10N. sodium hydroxide to precipitate a white solid. The solid was filtered and washed with water and purified by Gilson HPLC to give the desired product (93 mg) MS m/z=477 (M+H).
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