Methanol → 3-[(1S,2S)-2-Hydroxycyclohexyl]-6-[(6-methoxypyridin-3-yl)methyl]pyrido[3,4-h]quinazolin-4(3H)-one

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Reaction Conditions

Reaction Steps

To a solution of 6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclohexyl]pyrido[3,4-h]quinazolin-4(3H)-one (Example 1, 0.060 g, 0.14 mmol) in 2 mL of methanol under an atmosphere of nitrogen was added trans-N,N′-dimethylcyclohexane-1,2-diamine (6.0 mg, 0.042 mmol) and copper(I) iodide (6.0 mg, 0.033 mmol). The mixture was heated at 150° C. for 15 h in a sealed pressure vessel, cooled to rt, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-5% methanol in dichloromethane, to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 417.0 for [M+H]+: 1H NMR (400 MHz, CD3OD) δ 9.41 (s, 1H), 8.68 (s, 1H), 8.60-8.54 (m, 1H), 8.36-8.28 (m, 2H), 8.09 (s, 1H), 8.05 (s, 1H), 7.40-7.38 (m, 1H), 6.66 (d, J=8.3 Hz, 1H), 4.58 (br s, 1 H), 4.47 (s, 2H), 4.09 (br s, 1H), 3.90 (s, 3H), 2.61 (br s, 1H), 2.30-2.27 (m, 1H), 2.05-1.92 (m, 4H), 1.40-1.32 (m, 2H).

Provenance & Evidence