Diisopropylethylamine → HCID 58458903, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(benzyloxy)-2-ethoxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid (0.5045 g, 3 mmol), 2-(4-fluorophenyl)-N-hydroxyacetimidamide (0.9190, 3.02 mmol), HATU (1.255 g, 3.3 mmol) and DIEA (0.5 mL) in 1,4-dioxane (20 mL) was heated at 100° C. for 6 h. The mixture was cooled, diluted with EtOAc (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 7:3 Hexanes/EtOAc as eluant to afford the title compound product (0.68 g, 52% yield) as a yellow solid. 1HNMR (500 MHz, CDCl3) δ: 7.41-7.38 (2H, m), 7.30 (2H, dd, J=8.6, 5.2 Hz), 7.27-7.24 (3H, m), 6.99 (2H, t, J=8.6 Hz), 5.24 (2H, s), 4.52 (2H, q, J=7.0 Hz), 4.13 (2H, s), 3.47 (3H, s), 1.44 (3H, t, J=7.0 Hz). HRMS (M+H) calcd for C23H22N4O4F: 437.1625. found: 437.4719. Anal calcd for C23H21N4O4F: C, 63.29; H, 4.85; N, 12.83. found: C, 62.76; H, 4.84; N, 12.81.

Provenance & Evidence