1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-(benzyloxy)-3-(3,4-dimethoxybenzyl)-7-fluoro-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

Participants

Reaction Steps

A mixture of 1.0 g of the compound obtained in Step 4.5, 1.223 g of 4-nitrophenyl chloroformate and 0.915 g of DIEA in 15 ml of THF is irradiated in a microwave field for 15 minutes at 80° C. 0.616 g of DBU is then added and the mixture is stirred for 1 hour at room temperature. The reaction medium is evaporated under reduced pressure. The residue is taken up in EtOAc and washed twice with saturated aqueous NaHCO3 solution, then with aqueous 1M KHSO4 solution and then with water. The organic phase is dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (100/0, v/v) to (60/40, v/v) to give 0.74 g of the expected product.

Provenance & Evidence