Potassium Hydroxide → 2,4-Diamino-6-ethyl-5-(3-(6-(3-ethoxycarbonylpropoxy)-2-methylquinolin-4-yloxy)propoxy)pyrimidine

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Reaction Conditions

Reaction Steps

A mixture of 2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.308 g, 2.0 mmol), potassium hydroxide (0.123 g, 2.2 mmol) and 3-(6-(3-ethoxycarbonylpropoxy)-2-methylquinolin-4-yloxy)propyl bromide (0.821 g, 2.0 mmol) in DMF was stirred at 25° C. overnight. The DMF was evaporated to dryness and the residue was purified by column chromatography over silica gel (4% MeOH: 96% CH2Cl2 as eluent). The product was obtained as a light yellow solid (0.3578 g, 37%). 1H NMR (400 MHz, DMSO-d6): 0.90 (3H, t, J=7.5 Hz), 1.16 (3H, t, J=7.1 Hz), 2.08 (2H, m), 2.28 (4H, m), 2.48 (2H, t, J=7.0 Hz), 2.56 (3H, s), 3.86 (2H, t, J=5.8 Hz), 4.06 (4H, m), 4.41 (2H, t, J=5.8 Hz), 5.53 (2H, s), 6.11 (2H, s) 6.93 (1H, s), 7.31 (1H, dd, J=9.1, 2.6 Hz), 7.37 (1H, d, J=2.6 Hz), 7.76 (1H, d, J=9.1 Hz).

Provenance & Evidence