Trifluoroacetic acid → 4-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-ylamine

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (10.0 mL, 131.2 mmol, 20.0 eq) is added at 0° C. to a stirred solution of (4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-yl)-carbamic acid tert-butyl ester (2.50 g, 6.55 mmol, 1.0 eq) in dichloromethane (50 mL). After 20 hours stirring at 0° C., the reaction mixture is extracted with dichloromethane (3×200 mL) and water (200 mL) and the pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-ylamine as a light yellow solid (1.70 g, 92% yield).

Provenance & Evidence