Lithium Hydroxide → [3-(3,5-Dimethoxy-phenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy]-acetic acid

Participants

Reaction Steps

To a solution of ethyl 2-((3-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy)acetate (910 mg, 2.36 mmol) in dioxane (10 ml) and water (10 ml) was added LiOH (113 mg, 4.72 mmol) and the reaction mixture stirred at rt for 72 h. Then, water was added and the mixture extracted with CH2Cl2. The aqueous phase was then adjusted to pH ˜2 with aqueous 2M HCl. The resulting precipitate was then filtered off, washed with H2O and dried under vacuum to furnish 620 mg (74%) of the title compound. [1H-NMR (DMSO-d6, 600 MHz): δ 6.70 (br d, 2H), 6.55 (br s, 1H), 6.44 (s, 1H), 4.49 (s, 2H), 3.91 (s, 3H), 3.78 (s, 6H), 2.50 (s, 3H); UPLC-MS RtJ=0.93 min; [M+H]+=358.1]

Provenance & Evidence