Lithium hydroxide, monohydrate → 2,4-Diamino-6-ethyl-5-(3-(7-fluoro-2-methylquinolin-4-yloxy)propoxy)pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.5395 g, 3.5 mmol) and lithium hydroxide monohydrate (0.294 g, 7.0 mmol) in DMF (10 mL) was stirred at 25° C. for 1 hour after that 3-(7-fluoro-2-methylquinolin-4-yloxy)propyl bromide (1.043 g, 3.5 mmol) was added to the reaction mixture and the reaction mixture was left to stir at 25° C. overnight. Two thirds of the DMF was evaporated under vacuum and reaction mixture was poured in water, solid was separated by filtration and dried in oven at 80° C. The crude product was purified by column chromatography on silica gel (4% MeOH: 96% CH2Cl2 as eluent). The product was obtained as white crystalline solid (0.6629 g, 51%). 1H NMR (400 MHz, DMSO-d6): 0.89 (3H, t, J=7.5 Hz), 2.28 (4H, m), 2.60 (3H, s), 3.85 (2H, t, J=5.9 Hz), 4.42 (2H, t, J=5.9 Hz), 5.57 (2H, s), 6.15 (2H, s), 6.99 (1H, s), 7.39 (1H, dt, J=8.8, 2.5 Hz), 7.57 (1H, dd, J=10.8, 2.5 Hz), 8.15 (1H, dd, J=9.1, 6.4 Hz).

Provenance & Evidence