[CH3:1][N:2]([CH3:35])[C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([NH:21][CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[C:14]([O:19][CH3:20])[CH:13]=3)[CH:6]=[CH:5][N:4]=1.[ClH:36].C(OCC)C>O1CCOCC1>[ClH:36].[CH3:20][O:19][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[CH:18]=[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([N:2]([CH3:35])[CH3:1])[N:8]=1)[CH:10]=[C:11]2[NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1To a solution of tert-butyl 4-((3-(2-(dimethylamino)pyrimidin-4-yl)-7-methoxynaphthalen-1-yl)amino)piperidine-1-carboxylate (142) (215 mg, 0.45 mmol) in dioxane (6 ml) was added 4 M hydrochloric acid in dioxane (3 ml). The mixture was stirred at room temperature for 24 hours. Diethylether (100 ml) was added and the solid isolated by centrifugation. The solid was washed with diethylether (2×50 ml) and dried under vacuum to give 4-(6-methoxy-4-(piperidin-4-ylamino)naphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (143) as a pale yellow/orange solid (196 mg). LCMS m/e 378 (M+H)
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