Ethyl Acetate → HCID 178524881, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (403) (900 mg. 1.8 mmol) in a mixture of tetrahydrofuran:water (2:1) (30 mL) was added lithium hydroxide monohydrate (756 g, 18.0 mmol) and the mixture was refluxed for 24 h (TLC, ethyl acetate, Rf=0.1). After completion of reaction, volatiles were evaporated and the aqueous part was washed with ethyl acetate (3×30 mL). The aqueous layer was acidified with HCl (6N) to pH 3 and extracted with ethyl acetate (3×50 mL). The organic phase was thereafter dried and concentrated to get 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl methyl)-pyrimidine-4-carboxylic acid (404) (500 mg, 62%) as an off-white sticky solid.

Provenance & Evidence