Sodium Carbonate → 5-(2-(1H-pyrazol-4-yl)ethoxy)-3-methyl-7-(4-morpholinophenyl)pyrido[4,3-d]pyrimidin-4(3H)-one

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Reaction Conditions

Reaction Steps

To a solution of 5-(2-(1H-pyrazol-4-yl)ethoxy)-7-chloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (31.6 mg, 0.10 mmol) in 1,4-dioxane (1 mL) were added 4-morpholinophenylboronic acid pinacol ester (29.9 mg, 0.10 mmol), 2M aqueous Na2CO3 solution (155 μL, 0.30 mmol), and a catalytic amount of Pd(dppf)2Cl2. The reaction mixture was purged with N2 and heated at 140° C. by a microwave reactor for 15 minutes. The mixture was then cooled, quenched with H2O and extracted with EtOAc. The combined organic layer was dried over MgSO4, concentrated, and purified by silica gel chromatography (eluent: 0-10% MeOH in DCM) to provide the title compound as a yellow solid. 1H NMR (CD3OD, 400 MHz) δ 8.37 (s, 1H), 8.06 (d, J=9.2 Hz, 2H), 7.71 (s, 2H), 7.43 (s, 1H), 7.04 (d, J=9.2 Hz, 2H), 4.71 (t, J=6.4 Hz, 2H), 3.85 (t, J=4.8 Hz, 4H), 3.55 (s, 3H), 3.27 (t, J=4.8 Hz, 4H), 3.10 (t, J=6.4 Hz, 2H); ESI-MS m/z 433.1 (MH+).

Provenance & Evidence