5-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-yloxy)-N-(4-chlorophenyl)-6-methylisoquinolin-1-amine → HCID 178422909, compound

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Reaction Steps

A solution of 5-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-yloxy)-N-(4-chlorophenyl)-6-methylisoquinolin-1-amine (0.22 g, 0.37 mmol) in TFA (5 mL) was stirred in a 65° C. oil bath for 3.5 h. The TFA was removed in vacuo and the residue was dissolved in MeOH (50 mL) and 2 M NH3 in MeOH (50 mL) and adsorbed onto a pad of silica gel. The crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with a gradient of 1% to 8% 1 M NH3.MeOH in CH2Cl2 (over 20 min), to give 5-(3-(9H-purin-6-yl)pyridin-2-yloxy)-N-(4-chlorophenyl)-6-methylisoquinolin-1-amine as a white solid. 1H NMR (400 MHz, DMSO-d6) □ ppm 2.23 (s, 3H), 7.24-7.33 (m, 2H), 7.35 (d, J=8.53 Hz, 2H), 7.53 (d, J=8.53 Hz, 1H), 7.88-7.97 (m, 3H), 8.13 (d, J=5.02 Hz, 1H), 8.24 (d, J=7.53 Hz, 1H), 8.34 (d, J=8.53 Hz, 1H), 8.68 (s, 1H), 9.07 (s, 1H), 9.27 (s, 1H), 13.64 (s, 1H); MS (ESI, pos. ion) m/z: 480.1 [M+H]+

Provenance & Evidence