[CH:1]1([NH:4][C:5](=[O:43])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][C@@H:37]4[CH3:42])[C:16]4[CH2:21][N:20]([CH2:22][CH:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)[CH2:19][C:17]=4[N:18]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl.CO>O1CCOCC1>[CH:1]1([NH:4][C:5]([NH:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:14]=[C:15]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][C@@H:37]4[CH3:42])[C:16]4[CH2:21][N:20]([CH2:22][CH:23]5[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]5)[CH2:19][C:17]=4[N:18]=3)=[CH:11][CH:12]=2)=[O:43])[CH2:3][CH2:2]1(S)-tert-butyl 4-((2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)methyl)piperidine-1-carboxylate (example 128) (24 mg, 0.04 mmol) was stirred in a solution of 4M HCl in dioxane (1 mL), and methanol (0.5 mL) until analysis by LCMS indicated reaction was complete. Reaction mixture was then purified by TsOH cartridge (loaded in MeOH eluted with 2M methanolic ammonia) to afford an orange brown solid (4.9 mg, 0.009 mmol, 25%).
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