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

Participants

Reaction Conditions

Reaction Steps

To an EtOH (10 mL) solution of ethyl 6-cyclopropyl-1-(1-cyclopropylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (720 mg, 2.297 mmol) was added sodium hydroxide (6.89 mL, 6.89 mmol) and the mixture heated at 70° C. for 1 hour. The solvent was removed in vacuo and the residue was dissolved in 20 mL of water. The contents were acidified 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. The final product was collected as a solid, 0.560 g (85%). LCMS E-S (M+H)=286.3 1H NMR (400 MHz, DMSO-d6) δ ppm 0.15-0.33 (m, 2H), 0.38 (dq, J=9.57, 4.89 Hz, 1H), 0.50-0.65 (m, 1H), 0.90-1.10 (m, 4H), 1.27-1.42 (m, 1H), 1.57 (d, J=6.82 Hz, 3H), 2.23-2.36 (m, 1H), 2.57 (s, 3H), 4.18 (dq, J=9.32, 6.83 Hz, 1H), 7.44 (s, 1H), 12.79 (br. s., 1H).

Provenance & Evidence