N,N-Dimethylethylenediamine → 1-(3-Tert-butylphenyl)-3-(5-(2-(2-(dimethylamino)ethylamino)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl)urea

Participants

Reaction Steps

Using a procedure analogous to Example A1, 1-(3-tert-butylphenyl)-3-(2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.200 g, 0.407 mmol) and N,N-dimethylethylenediamine (0.181 mL, 1.65 mmol) were combined to afford 1-(3-tert-butylphenyl)-3-(5-(2-(2-(dimethylamino)ethylamino)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl)urea (0.150 g, 86% yield) as a light yellow solid. It was converted to corresponding HCl salt by reacting with HCl (4.0 M HCl in dioxane, 1.0 eq.). 1H NMR (400 MHz, DMSO-d6): δ 9.28 (s, 1H), 8.73 (s, 1H), 8.64 (d, J=1.6 Hz, 1H), 8.39 (d, J=7.6 Hz, 1H), 8.04 (s, 1H), 7.93 (s, 1H), 7.43 (s, 1H), 7.28-7.24 (m, 3H), 7.18 (t, J=8.0 Hz, 1H), 6.99 (tt, J=7.6, 0.8 Hz, 1H), 3.74 (broad, 2H), 3.63 (s, 3H), 3.30 (broad, 2H), 2.81 (d, J=4.8 Hz, 6H), 1.25 (s, 9H); MS (ESI) m/z: 532.3 (M+H+).

Provenance & Evidence