Sodium hydride → 1-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

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Reaction Steps

Prepared according to Procedure I using 8-chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinoline (0.235 g, 0.73 mmol), NaH (0.047 g 60% in oil, 1.17 mmol, 1.6 eq) and 3-iodo-1H-pyrazolo{3,4-d}pyrimidin-4-amine (0.209 g, 0.8 mmol, 1.1 eq) in DMF. 1-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine was obtained after purification as a white solid [PI3KδIC50=14 nM]. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (1 H, s), 8.09 (1 H, dd, J=8.6, 1.2 Hz), 7.98-8.05 (2 H, m), 7.66 (1 H, t), 7.48 (1 H, dd, J=8.2, 0.8 Hz), 7.36 (1 H, dt, J=7.8, 1.6 Hz), 7.25 (1 H, dt, J=7.4, 1.2 Hz), 7.13 (1 H, dd, J=7.4, 1.6 Hz), 5.53 (2 H, s) Mass Spectrum (ESI) m/e=547.0 and 549.0 (M+1)

Provenance & Evidence