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Reagents and conditions: (a) BH3·THF, THF, 0 °C, 1 h; (b) MsCl, TEA, DCM, 0 °C, 0.3 h; (c) NaN3, DMF, 50 °C, 15 h; (d) H2, 10%Pd/C, ethanol, RT, 3.5 h; (e) N-(benzyloxycarbonyloxy) succinimide, DCM, RT, 12 h; (f) TFA, RT, 0.5 h; (g) 4-chloro-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (47), 2-propanol, DIPEA, 85 °C, 7 h; (h) 6N HCl, methanol, 60 °C, 1 h.
