Triethylamine → 6-Bromo-4-chloro-quinazoline

Participants

Reaction Steps

To a suspension of 6-Bromo-3H-quinazolin-4-one (1.5 g, 6.65 mmole) in 1,4-dioxane (30 ml) under nitrogen was added triethylamine (2.8 ml, 19.9 mmole). The resulting suspension was rapidly stirred while phosphorous oxychloride (1.85 ml, 19.9 mmole) was added over 5 minutes. The reaction was stirred at room temperature for 5 minutes, then heated at 80° C. for 30 minutes, when no starting material was detectable by LC/MS. After cooling to room temperature, the reaction mixture was concentrated in vacuo. The resulting residue was partitioned between ethyl acetate and water. The insoluble material was collected by filtration and washed with water. The layers of the filtrate where separated and the organic layer was washed twice with water and once with brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The resulting solid was combined with the collected precipitate and the mixture was recrystallized from ethyl acetate/hexanes to give 760 mg after drying in vacuo. The resulting compound was characterized as follows: masspectrometry: M/Z=244; HPLC: method A, Rt 1.51 minutes.

Provenance & Evidence