Sodium Hydroxide → HCID 178434033, compound

Participants

Reaction Steps

Sodium hydroxide (52.6 mL, 52.6 mmol) was added to an EtOH solution (100 mL) of ethyl 1-(1,1-dimethylethyl)-3-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (7.3 g, 26.3 mmol) and stirred at room temperature for 16 h. The solvent was removed in vacuo. The crude residue was suspended in water, and extracted with EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered, and concentrated in vacuo. The solid product obtained was set aside. The aqueous phase was concentrated in vacuo and the crude product purified by reverse phase HPLC (mobile phase: 20-50% ACN/H2O, 0.1% TFA) to afford additional product. The combined products were collected as a solid, 5.76 g (88%). LCMS E-S (M+H)=250.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.5-13.9 (br s, 1H), 11.2-11.5 (br s, 1H), 6.78 (s, 1H), 2.46 (s, 3H), 1.70 (s, 9H).

Provenance & Evidence