Lithium hydroxide, monohydrate → (S)-2-Chloro-4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5-carboxylic acid

Participants

Reaction Steps

A solution of lithium hydroxide monohydrate (633 mg, 15.09 mmol) in water (6 mL) was added to a solution of (S)-ethyl 2-chloro-4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5-carboxylate (Preparation 5a, 490 mg, 1.51 mmol) in a mixture of methanol (6 mL) and tetrahydrofuran (2 mL) and the reaction mixture was stirred at ambient temperature for 3 hours. The solvents were evaporated under reduced pressure and water was added to the resulting residue. The pH was then adjusted to ca. 6 with 2M aqueous hydrochloric acid and the aqueous suspension was extracted with diethyl ether (×3). The organic phase was washed with water and brine, dried (MgSO4), filtered and the solvent evaporated under reduced pressure to give the title compound (0.21 g, 41%) as a semi-solid.

Provenance & Evidence