Aniline → HCID 136500839, compound

Participants

Reaction Steps

To 6-(2-chloroquinolin-8-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one hydrochloride (Example 19b; 0.075 g, 0.225 mmol) and aniline (0.144 ml, 1.576 mmol) was added LHMDS (1.0 M in THF; 1.576 ml, 1.576 mmol). After 1 h the reaction was partitioned between saturated aq. NH4Cl and EtOAc. The aq. layer was washed with saturated aq. NH4Cl and 1× brine, dried over Na2SO4, and concentrated in vacuo. The solid residue from the separatory funnel was rinsed with 10% DCM/MeOH into an Erlenmeyer flask, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The resulting solid was suspended in MeOH and filtered. The solid was collected to give 6-(2-(phenylamino)quinolin-8-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (0.012 g, 0.034 mmol, 15% yield) as a dull-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (1H, br. s), 11.80 (1H, br. s.), 9.59 (1H, s), 8.13 (1H, d, J=9.0 Hz), 8.02 (1H, dd, J=7.4, 1.6 Hz), 7.88 (1H, s), 7.78 (2H, dd, J=8.6, 1.2 Hz), 7.67-7.73 (1H, m), 7.28-7.38 (3H, m), 7.09-7.19 (2H, m), 6.97-7.05 (1H, m). m/z (ESI, +ve) 353.9 (M+H)+.

Provenance & Evidence