Sodium Iodide → HCID 178493869, compound

Participants

Reaction Conditions

Reaction Steps

N-(8-Hydroxy-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyrimidine-5-carboxamide (Intermediate B, 1.5 g, 4.4 mmol) was diluted in dimethylformamide (50 mL) containing a few drops of water. Cesium carbonate (7.24 g, 22.2 mmol) and sodium iodide (0.80 g, 5.3 mmol) were added, followed by tert-butyl (3-bromopropyl)carbamate (3.18 g, 13.3 mmol). The mixture was stirred at 100° C. overnight. After cooling to rt, the solvent was removed in vacuo. The residue was diluted in 10% methanol in dichloromethane, and solids were removed by filtration. The filtrate was concentrated and purified by silica gel flash column chromatography, eluting with 0-10% methanol in dichloromethane, to afford the title compound (1.13 g, 51%). 1H NMR (DMSO-d6+2 drops TFA-d) δ: 1.37 (9H, s), 1.94 (2H, m), 3.15 (2H, t), 4.03 (3H, s), 4.26 (4H, m), 4.57 (2H, m), 6.96 (1H, br t), 7.47 (1H, d), 7.82 (1H, m), 8.03 (1H, d), 8.79 (1H, m), 8.91 (1H, m), 9.46 (1H, m).

Provenance & Evidence