Ethanol → 2-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid

Participants

Reaction Steps

In the mixture of water (5 mL), ethanol (5 mL) and THF (15 mL) were dissolved ethyl 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylate (1.5 g, 3.9 mmol) and sodium hydroxide (260 mg, 6.5 mmol). The reaction was conducted at ambient temperature for 5 h. The solvent was removed by evaporation, followed by addition of water and washing with DCM. The aqueous phase was adjusted to a pH of 2 with dilute hydrochloric acid, and extracted with DCM. The organic phase was dried over sodium sulfate and concentrated to give 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-fluoro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid as a faint yellow solid (580 mg, 41.5% yield).

Provenance & Evidence