Hexyl isocyanate → N-hexyl-2,4-dioxo-5-(3-pyridyl)pyrimidine-1-carboxamide

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Reaction Steps

The title compound was obtained according, to the procedure described for the synthesis of Example 1, starting from 5-(3-pyridyl)-1H-pyrimidine-2,4-dione (0.067 g, 0,198 mmol). Herein, 2 equivalents of DMAP and 2.7 equivalents of hexyl isocyanate in 4 mL pyridine were used. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 40:60) to afford the title compound (0.04 g, 57%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.90 (t, J=6.0 Hz, 3H), 1.29-1.41 (m, 6H), 1.58-1.67 (m, 2H), 3.42 (dt, J=7.1, 5.5 Hz, 2H), 7.37 (ddd, J=8.0, 4.9, 0.9 Hz, 1H), 7.97 (td, J=8.0, 2.0 Hz, 1H), 8.64 (dd, J=4.9, 1.7 Hz, 1H), 8.66 (s, 1H), 8.80 (dd, J=2.4, 0.9 Hz, 1H), 9.11 (t, J=5.0 Hz, 1H), 9.21 (s, 1H). 13C NMR (101 MHz, CDCl3): δ 14.13, 22.66, 26.64, 29.29, 31.51, 41.58, 77.16, 113.74, 123.50, 127.93, 136.39, 136.58, 148.70, 149.48, 149.74, 151.09, 161.30. MS (ESI) m/z: 317 (M-Hr.

Provenance & Evidence