Barbituric Acid → rel-(2R,4R,4aR)-1,2,4,4a-tetrahydro-4-methyl-8-nitro-2-(trifluoromethyl)spiro[[1,4]oxazino[4,3-a]quinoline-5(6H), 5'(2'H)-pyrimidine]-2',4',6'(1'H,3'H)-trione

Participants

Reaction Conditions

Reaction Steps

2-[cis-2-methyl-6-(trifluoromethyl)morpholin-4-yl]-5-nitrobenzaldehyde (212 mg, 0.67 mol) is combined with barbituric acid (95 mg, 0.67 mmol, Aldrich) in a vial with MeOH (3 mL). The sealed reaction is heated to 80° C. on a shaker block for 21 hours and then the solvent is removed by rotary evaporation. The product is purified on a Biotage Flash 25M+ using a 26 minute linear gradient of 2.5%–10% MTBE in CH2Cl2 eluent. The product is dried under vacuum yielding a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01, 2.93, 3.46, 3.66, 3.73, 4.04, 4.40, 4.48, 7.10, 7.88, 8.01, 11.63, 11.94.

Provenance & Evidence