Sodium Hydroxide → 1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidine-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of methyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidine-3-carboxylate (160 mg, 0.38 mmol) in 10 mL of methanol was added a solution of sodium hydroxide (154 mg, 3.8 mmol) in 2 mL of water at room temperature. Then the reaction mixture was stirred at this temperature for 24 hours. Then solvent was evaporated at 40° C. at reduced pressure and the residue was suspended in 30 mL of THF, then treated with 2N HCl to pH=2. The solvent was evaporated and the residue was dissolved in 50 mL of THF, then filtered and the filtrate was evaporated to give 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidine-3-carboxylic acid (95 mg, 61.4%) as a yellow solid. LC-MS: 402.1 [M+H]+, tR=1.33 min.

Provenance & Evidence