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

Participants

Reaction Steps

2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.3963 g, 2.6 mmol) was added to a stirred solution of lithium hydroxide monohydrate (497.2 mg, 11.8 mmol) in DMF (2 mL) and the reaction mixture was stirred for 1 hour. A solution of 3-(quinolin-4-yloxy)-propyl mesylate (0.3868 g, 1.37 mmol) in DMF (1 mL) was slowly added and the reaction mixture was left stirring at 25° C. overnight. The reaction was diluted with dichloromethane and extracted with water. The dichloromethane layer was evaporated followed by crystallization of the residue from aqueous methanol. The product was obtained as a slightly yellow solid (0.4677 g, 53%). 1H NMR (400 MHz, DMSO-d6): 0.87 (3H, t, J=7.0 Hz), 2.24 (2H, q, J=7.0 Hz), 2.30 (2H, m), 3.85 (2H, t, J=5.5 Hz), 4.43 (2H, t, J=5.5 Hz), 5.53 (2H, s), 6.11 (2H, s), 7.06 (1H, d, J=5.2 Hz), 7.54 (1H, t, J=8.0 Hz), 7.72 (1H, ddd, J=1.4, 6.9, 8.3 Hz), 7.93 (1H, d, J=8.3 Hz), 8.15 (1H, d, J=8.5 Hz), 8.72 (1H, d, J=5.2 Hz).

Provenance & Evidence