Urea → HCID 135876054, compound

Participants

Reaction Conditions

Reaction Steps

(((E)-1-(4-hydroxy-3-methylphenyl)-3-(4-methylthiazol-5-yl)prop-2-en-1-one (200 mg, 0.77 mmol) and urea (0.23 g, 3.8 mmol) were suspended in 5 mL of 4N HCl solution in dioxane (Aldrich), and the reaction mixture was heated in a sealed vessel to 120° C. for 20 h. After cooling to room temperature, the resulting mixture was concentrated in vacuo to remove dioxane. The residue was dissolved in 5 mL of methanol, and the product was purified by preparative HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to yield 7.7 mg of 4-(4-hydroxy-3-methylphenyl)-6-(4-methyl-1,3-thiazol-5-yl)pyrimidin-2(1H)-one. 1H NMR (400 MHz, d6-DMSO): δ 9.11 (s, 1H), 7.81 (d, 1H), 7.72 (dd, 1H), 7.07 (s, 1H), 6.90 (d, 1H), 2.73 (s, 3H), 2.17 (s, 3H). MS (EI) for C15H13N3O2S: 300.4 (MH+).

Provenance & Evidence