Sodium Hydroxide → 6-Cyclopropyl-1-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid
Reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:17]([O:19]CC)=[O:18])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]([CH3:16])[CH3:15])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:17]([OH:19])=[O:18])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]([CH3:16])[CH3:15])[C:8]=3[N:9]=2)[CH2:2][CH2:3]1Participants
4
Procedure
To a solution of ethyl 6-cyclopropyl-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (200 mg, 0.696 mmol) in ethanol (5 mL) was added sodium hydroxide (2.088 mL, 2.088 mmol), and the mixture stirred at room temperature for 30 min. The reaction mixture was concentrated in vacuo. The residue was diluted with water (30 mL) and then acidified with acetic acid. The contents were extracted with DCM (3×30 mL). The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The final product was obtained as 0.17 g (94%). LCMS E-S (M+H)=260.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97-1.12 (m, 4 H) 1.44 (d, J=6.57 Hz, 6 H) 2.27-2.38 (m, 1 H) 2.55 (s, 3 H) 5.07 (quin, J=6.69 Hz, 1 H) 7.43 (s, 1 H) 13.30-14.08 (m, 1 H).