Ethanol → HCID 58504528, compound

Participants

Reaction Conditions

Reaction Steps

In a sealable tube, 2-(ethyloxy)-6-fluoro-4-{2-(methylamino)-6-[(2R)-2-methyl-1-pyrrolidinyl]-4-pyrimidinyl}benzonitrile (87 mg, 0.245 mmol), EtOH (5 mL), Hunig's base (0.046 mL, 1.469 mmol), and hydrazine anhydrous (0.043 mL, 0.245 mmol) were added, and the yellow suspension mixture was heated at 100° C. overnight in an oil bath. After overnight, there was a yellow solution as well as a little amount of white colored solid formed. LCMS showed no more starting material. The reaction was cooled to room temperature. Water (20 mL) was added to the yellow solution, and a solid was formed. The solid was filtered, washed by water, and dried in vacuum. The solid was purified by flash column chromatography. The fractions containing product were combined, and the solvent was removed under reduced pressure to afford the title compound (48 mg) as a white solid. LC-MS (ES) m/z=368 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.21 (d, J=6.1 Hz, 3H), 1.44 (t, J=7.0 Hz, 3H), 1.66 (m, 1H), 2.02 (m, 3H), 2.82 (d, J=4.8 Hz, 3H), 3.56 (m, 1H), 4.12-4.24 (q, J=7.1 Hz, 2H), 4.99 (s, 2H), 6.19 (s, 1H), 6.32-6.51 (m, 1H), 6.87-6.98 (m, H), 7.41-7.56 (m, 1H), 11.50 (s, 1H).

Provenance & Evidence