Ethanol → HCID 178490274, compound

Participants

Reaction Conditions

Reaction Steps

In a sealed tube are combined 3-dimethylamino-1-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-but-2-en-1-one [147 mg, 0.33 mmol, Intermediate (47) prepared as described in Example 38, Step 1], hydrazine hydrate (200 μL), and EtOH (3 mL). Heated the mixture to 85° C. and stirred for 1.5 hours. The reaction mixture is concentrated to provide an oil which is subjected to flash column chromatography on silica gel eluting with 20 to 60% EtOAc in heptane gradient, to afford {2-methoxy-6-[3-(5-methyl-2H-pyrazol-3-yl)-phenyl]-pyrimidin-4-yl}-[2-(4-methoxy-phenyl)-ethyl]-amine [136 mg, 99%, Example 39]. LCMS: RT=2.79 minutes, MS: 416 (M+H). 1H NMR (300 MHz, CDCl3) δ 8.29 (1H, s), 7.9 (1H, d, J=0.027 Hz), 7.72 (1H, d, J=0.025 Hz), 7.4 (1H, t, J=0.026 Hz), 7.09 (2H, d, J=0.028 Hz), 6.82 (2H, d, J=0.028 Hz), 6.35 (2H, d, J=0.024 Hz), 5.18 (1H, s), 3.98 (3H, s), 3.75 (3H, s), 3.59 (2H, m), 2.83 (2H, t, J=0.023), 2.3 (3H, s).

Provenance & Evidence