Diisopropylethylamine → HCID 58458927, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(benzyloxy)-1-methyl-2-morpholino-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid (prepared according to the procedure in WO2004062613 (0.35 g, 1 mmol), 2-(4-fluorophenyl)-N-hydroxyacetimidamide (0.25, 1.5 mmol) HATU (0.76 g, 2 mmol), DIEA (0.35 mL) and DMAP (10 mg) in 1,4-dioxane (5 mL) was heated at 110° C. for 5 h. The mixture was cooled, diluted with Et2O (50 mL), washed with water (10 mL), sat. NaHCO3 (10 mL), brine (10 mL) then dried (Na2SO4), filtered and concentrated to give a brown residue. This residue was purified by flash chromatography on a silica gel column using 1:1 hexanes/EtOAc as eluant to afford the title compound (0.24 g, 50% yield) as a white solid. 1HNMR (500 MHz, CDCl3) δ: 7.42-7.39 (2H, m), 7.32 (2H, dd, J=8.4, 5.4 Hz), 7.28-7.25 (3H, m), 7.00 (2H, t, J=8.6 Hz), 5.28 (2H, s), 4.14 (2H, s), 3.84-3.82 (4H, m), 3.55 (3H, s), 3.24-3.22 (4H, m). HRMS (M+H) calcd for C25H25N5O4F: 478.1491. found: 478.5663.

Provenance & Evidence