4-Quinazolin-4-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester → 4-(1,2,3,6-Tetrahydro-pyridin-4-yl)-quinazoline

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Reaction Steps

To a stirred solution of 4-Quinazolin-4-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester (0.907 g, 2.63 mmol) in MeOH (30 mL) under N2 was cautiously added 10% Pd on carbon (100 mg). The reaction was hydrogenated at 50 psi using a parr shaker for 3 days. The catalyst was removed by filtration. The filtrate was evaporated under vacuum. The resulting residue was purified by column chromatography (DCM:MeOH, 20:1 to DCM:MeOH:Et3N, 100:10:1) to give 4-(1,2,3,6-Tetrahydro-pyridin-4-yl)-quinazoline (0.358 g, 64%) as a white waxy solid. 1H NMR (CDCl3, 400 MHz) δ 9.27 (s, 1H), 8.19 (d, J=8.4 Hz, 1H), 8.06 (d, J=8.4 Hz, 1H), 7.88 (t, J=8.4 Hz, 1H), 7.65 (t, J=8.4 Hz, 1H), 3.71 (m, 1H), 3.31 (m, 2H), 2.90 (m, 2H), 1.99 (m, 4H). LCMS (APCI+) m/z 214 [M+H]+; Rt=1.60 min.

Provenance & Evidence