Cesium carbonate → HCID 14116711, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of dimethyl 4-bromoisophthalate (0.25 g, 0.92 mmol) and methylurea (88.2 mg, 1.19 mmol) in 1,4-dioxane (5 mL) was added cesium carbonate (0.60 g, 1.83 mmol). 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (53.0 mg, 0.092 mmol) was then added followed by tris(dibenzylideneacetone)dipalladium (0) (42 mg, 0.046 mmol). The reaction mixture was heated to 100° C. and stirred for 2 d. The mixture was then cooled to rt and concentrated. Water was added and the remaining solid was filtered. The collected solid was then washed with DCM (3×) to afford methyl 3-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-6-carboxylate (0.17 g, 80%). LC-MS: (FA) ES+ 235; 1H NMR (400 MHz, DMSO) δ 11.81 (s, 1H), 8.47 (d, J=2.0 Hz, 1H), 8.16 (dd, J=8.6, 2.0 Hz, 1H), 7.25 (d, J=8.6 Hz, 1H), 3.87 (s, 3H), 3.26 (s, 3H).

Provenance & Evidence