Methanol → HCID 67521556, compound

Participants

Reaction Steps

A solution of 2-[(3-nitro[1,5]naphthyridin-4-yl)amino]ethanol (6.34 g, 27.1 mmol) dissolved in 25 mL of pyridine was treated with tert-butyldimethylsilyl chloride (4.50 g, 29.8 mmol) and N,N-dimethylaminopyridine (331 mg, 2.71 mmol) and the mixture was stirred under N2. After 3 hours, the reaction mixture was treated with 10 mL of methanol and then concentrated to give a yellow solid. The resulting solid was dissolved in 100 mL of ethyl acetate and washed with H2O (3×50 mL) and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to give a yellow powder. Crystallization from 50 mL of 1:1 hexane/ethyl acetate gave 7.28 g of N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-nitro[1,5]naphthyridin-4-amine as a yellow solid.

Provenance & Evidence