Benzoyl chloride → 5-benzoyl-1,3,6-trimethyl-2,4(1H,3H)-Pyrimidinedione

Participants

Reaction Steps

A mixture of 1,3,6-trimethyl-compound 2 (12.3 g, 80 mmol), benzoyl chloride (11.5 g, 9.5 mL, 82 mmol) and anhydrous zinc chloride (10.8 g, 79 mmol) in toluene (100 mL) was heated to reflux for 6 h. The mixture was poured over ice (200 g), and the separated toluene layer was concentrated in vacuo. The crude residue was purified by flash chromatography to yield 3 (5.8 g, 28%): mp 132-134° C.; MS (ES+) (m/z): [M+1]+ calculated for C14H15N2O3, 259.28. found 259.09. This compound matched analytical data as reported (see, e.g., Tsupak et al., Khimiya Geterotsiklicheskikh Soedinenii. 7:1096-1102 (2003)).

Provenance & Evidence