[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([CH2:16][C:17](OC)=[O:18])=[N:8]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[OH-].[Na+]>O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([CH2:16][CH2:17][OH:18])=[N:8]1To a solution methyl [1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate (128 mg, 0.465 mmol) at 0° C. was added 2M LAH in THF (232 ul, 0.465 mmol) and stirred at 0° C. for 30 minutes. After this time, the reaction mixture was sequentially treated with water (18 ul) and 1.0N NaOH (54 ul) and stirred at 25° C. for 30 minutes. After this time, the mixture was filtered through celite and rinsing with THF. The filtrates were combined and the solvent evaporated in vacuo. The residue was purified by chromatography using RediSep column (12 g) and eluting with a gradient of 0-10% MeOH/CH2Cl2 to give the title compound. LRMS (M+1): 164.0.
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