Thionyl Chloride → 3-(Chloromethyl)-N,1-bis(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amine

Beteiligte Stoffe

Reaktionsschritte

To a slurry of {1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methanol (1.49 g, 3.68 mmol) in chloroform (15 mL) cooled in an ice bath was added thionyl chloride (538 μL, 7.37 mmol). The resulting mixture was then allowed to warm to room temperature and left at room temperature for 30 minutes. The reaction was determined by LCMS monitoring not to be complete not complete, so the reaction mixture was re-cooled in an ice bath, treated with additional thionyl chloride (100 μL), and then stirred at room temperature for 30 minutes. The reaction mixture was then poured into aqueous NaHCO3, extracted into CHCl3 and the solvent removed in vacuo. This residue was purified on a silica gel (120 g) column (0-60% EtOAc/CHCl3 to give the title compound. LRMS (M+1)=422.9

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