Sodium Hydroxide → 1-Amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Participants

Reaction Steps

To a solution of ethyl 1-amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (100 mg, 0.406 mmol) in ethanol (10 mL) was added sodium hydroxide (1 ml, 0.406 mmol), and the mixture stirred at room temperature for 2 h. The solvent was removed in vacuo, and the residue diluted with EtOAc (30 mL) and water (20 mL). The reaction mixture was acidified to pH 3 with citric acid. The phases were separated and the aq. phase extracted with EtOAc (4×20 mL). The combined organic layers were washed with water, dried over MgSO4, filtered, and concentrated in vacuo. The final product was collected as 0.075 g (84%). LCMS E-S (M+H)=219.5. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00-1.13 (m, 4 H), 2.27-2.45 (m, 1 H), 6.36 (s, 2 H), 7.60 (s, 1 H), 8.06 (s, 1 H), 13.81 (br. s., 1 H).

Provenance & Evidence