Urea → HCID 22473437, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromobenzaldehyde (13.0 g, 70 mmol), acetoacetamide (7.08 g, 70 mmol), urea (5.26 g, 87.5 mmol), polyphosphate ester (9.1 g, 21 mmol) and THF (150 mL) was heated in a sealed tube for 18 h at 75° C. This mixture was cooled to room temperature; more polyphosphate ester (60.6 g, 140 mmol) was added and heating resumed for another 5 h. The reaction mixture was cooled to room temperature, poured into water (800 mL) and stirred for 18 h. The resulting precipitates were collected by vacuum filtration, washed with water and with ether, and air dried to yield 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-(2H)-pyrimidine as a light yellow solid (16.25 g; 79%): 1H NMR (DMSO-d6, 400 MHz) δ 9.60 (s, 1H), 7.87 (s, 1H), 7.55 (m, 1H), 7.48 (m, 1H), 7.39 (t, 1H, J=7.9 Hz), 7.32 (d, 1H, J=7.9 Hz), 5.14 (s, 1H), 2.02 (s, 3H).

Provenance & Evidence