Sodium Carbonate → 7-(6-(2-hydroxypropan-2-yl)pyridin-3-yl)-5-(isopropylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

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Reaction Conditions

Reaction Steps

A mixture of crude 7-chloro-5-(isopropylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (455 mg, ˜1.80 mmol), crude 2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)propan-2-ol (570 mg, ˜2.10 mmol), Pd(PPh3)4 (208 mg, 0.18 mmol) and Na2CO3 (1.90 g, 18.0 mol) in a mixed solvent of dioxane (30 mL) and H2O (10 mL) was purged with N2, heated at 90° C. for 16 hours, poured into water (400 mL) and extracted with EtOAc (5×70 mL). The combined organic phases were washed with brine (20 mL), dried over Na2SO4, and evaporated to result in a residue that was subjected to chromatography with gradient mixed solvents from DCM/MeOH/28% aqueous NH4OH (24:10:1) to (15:10:1) to afford the title compound. 1H NMR (DMSO-d6) 1.29 (d, J=6.4 Hz, 6H, 2CH3), 1.47 (s, 6H, 2CH3), 3.44 (s, 3H, NCH3), 4.42 (m, 1H), 5.30 (s, 1H, OH), 7.23 (s, 1H), 7.76 (d, J=8.4 Hz, 1H), 8.44 (d, J=8.4 Hz, 1H), 8.45 (s, 1H), 8.75 (d, J=6.8 Hz, 1H, NH), 9.22 (s, 1H); ESI-MS m/z 354.2 (MH+); Anal. Calcd for C19H23N5O2: C, 64.57; H, 6.56; N, 19.82. Found: C, 64.39; H, 6.47; N, 19.75.

Provenance & Evidence