Methanol → 1-{1-[4-(3-phenyl-5-pyrimidin-2-ylpyridin-2-yl)benzyl]piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

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Reaction Steps

A mixture of crude 2-{6-[4-(bromomethyl)phenyl]-5-phenylpyridin-3-yl}pyrimidine (0.050 g, 0.124 mmol), 1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.030 g, 0.137 mmol), and DIEA (0.065 mL, 0.373 mmol) in 1:1 MeOH:THF (1 mL) was stirred for 1 hr. Reaction concentrated and the residue was purified by reverse phase HPLC (5% CH3CN: 95% H2O: 0.01% TFA to 95% CH3CN: 5% H2O: 0.01% TFA) to give the title compound. 1H-NMR (500 MHz, d6 DMSO) δ 9.77 (bs, 1H), 9.60 (d, 1H, J=2.0 Hz), 9.00 (d, 2H, J=4.9 Hz), 8.70 (bs, 1H), 8.68 (d, 2H, J=2.0 Hz), 8.45 (bs, 1H), 8.37 (s, 1H), 8.30 (s, 1H), 7.58 (t, 1H, J=4.9 Hz), 7.54-7.37 (m, 9H), 5.05-4.93 (m, 1H), 4.35 (s, 2H), 3.49 (d, 2H, J=11.23 Hz), 3.37-3.21 (m, 2H), 2.47-2.33 (m, 2H), 2.15 (d, 2H, J=11.7 Hz) HRMS m/z (M+H) Calcd: 540.2619, found: 540.2616.

Provenance & Evidence