Sodium Hydroxide → 6-Cyclopropyl-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Participants

Reaction Steps

To an EtOH solution (30 mL) of ethyl 6-cyclopropyl-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (300 mg, 0.911 mmol) was added sodium hydroxide (1.82 mL, 1.82 mmol) and the mixture stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was dissolved in 20 mL of water. The contents were acidifed with acetic acid, and extracted with EtOAc (4×30 mL). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the final product as 265 mg (97%). LCMS E-S (M+H)=302.4 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.09 (m, 4 H), 1.81 (dd, J=12.38, 2.27 Hz, 2 H), 2.15 (qd, J=12.25, 4.42 Hz, 2 H), 2.28-2.37 (m, 1 H), 2.54 (s, 3 H), 3.46-3.60 (m, 2 H), 3.89-4.02 (m, 2 H), 4.91 (m, J=11.56, 11.56, 4.17, 4.04 Hz, 1 H), 7.42 (s, 1 H), 13.73 (br. s., 1 H).

Provenance & Evidence