6-[(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)(methyl)amino]-2-chloro-5-fluoronicotinonitrile → 2-Chloro-5-fluoro-6-[(3-hydroxypropyl)(methyl)amino]nicotinonitrile

Participants

Reaction Steps

A mixture of 6-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(methyl)amino]-2-chloro-5-fluoronicotinonitrile (Example 310, 0.73 g, 2.04 mmol) in ethanol/HCl/water (95:1:4) (50 mL) was stirred at rt for 18 h, and then concentrated under reduced pressure. The residue was passed through a plug of silica gel with ethyl acetate as the eluent to give the product (0.5 g, 100%) as a waxy yellow solid. 1H NMR (400 MHz, CD3OD) δ 7.54 (d, 1H), 3.65 (dt, 2H), 3.54 (t, 2H), 3.18 (d, 3H), 1.85-1.77 (m, 2H).

Provenance & Evidence