Furan → HCID 178441855, compound

Participants

Reaction Steps

To a stirred solution of 7.88 ml of furan in 80 ml of dry tetrahydrofuran is cooled at 0° C. and 47.8 ml of n-butyl lithium (2.5 M in hexanes) is added dropwise. Stirring is continued for 1 hour at 0° C. and the mixture allowed to warm to room temperature. The reaction mixture is cooled to -78° C. and 5.0 g of 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxaldehyde added rapidly. The reaction mixture is stirred for 1.5 hours at -78° C., quenched with 100 ml of saturated ammonium chloride, allowed to warm to room temperature and the volatiles removed in vacuo. The reaction mixture is diluted with 500 ml of ethyl acetate and washed with water, 2N citric acid, 1M sodium bicarbonate and brine. The organic layer is dried and evaporated to a residue which crystallizes from ethyl acetate to afford 3.75 g of the desired product, m.p. 183°-185° C. An additional 700 mg of the desired product is obtained from the filtrate as white crystals m.p. 183°-185° C. Fab Mass Spec 299 (M+H).

Provenance & Evidence