Triethylamine → 2-[(4-Fluorophenyl)methyl]-9-hydroxy-7-[(1-morpholinocyclopentyl)methyl]-3,4-dihydropyrazino[1,2-c]pyrimidine-1,6,8-trione

Participants

Reaction Steps

To a solution of 1-{[4-(4-fluorobenzyl)-3-oxopiperazin-1-yl]carbonyl}-3-methyl-1H-imidazol-3-ium iodide (75 mg, 0.17 mmol) in 1 mL of anhydrous DMF, under an atmosphere of nitrogen, was added triethylamine (28 μL, 0.20 mmol) and [(1-morpholin-4-ylcyclopentyl)methyl]amine (37 mg, 0.20 mmol) and stirred overnight at room temperature. Dimethyl oxalate (100 μL of 6.76 M DMF solution, 0.67 mmol) and sodium hydride (16 mg, 0.67 mmol) were added, and the reaction mixture was stirred at room temperature. The reaction was quenched with 4 mL of aq NH4Cl, diluted with water, followed by dropwise addition of 1N HCl until slightly acidic. The precipitated product was collected by filtration and rinsed with water, and diethyl ether. Drying under high vacuum provided the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.84 (s, 1H), 7.41 (dd, J=8.5, 5.6 Hz, 2H), 7.17 (bt, J=8.8 Hz, 2H), 4.68 (s, 2H), 4.06 (bs, 2H), 3.94 (bs, 2H), 3.59 (t, J=5.2 Hz, 2H), 3.51 (t, J=4.1 Hz, 4H), 2.64 (t, J=4.1 Hz, 4H), 1.7-1.4 (m, 8H). HRMS ES (M+1) calc'd for C24H30N4O5F; 473.2195 m/z. found 473.2193 m/z.

Provenance & Evidence