N,N-Diethylaniline → HCID 67282409, compound

Participants

Reaction Conditions

Reaction Steps

Into a round bottom flask was added methyl 3-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (0.48 g, 2.1 mmol) dissolved in phosphoryl chloride (20.0 mL, 214 mmol). N,N-diethylaniline (0.99 mL, 6.2 mmol) was added followed by phosphorus pentachloride (0.22 g, 1.05 mmol). The reaction mixture was heated to 120° C. and stirred for 1 d. The mixture was then cooled to rt and concentrated. The residue was poured over ice and extracted with DCM (3×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was purified by flash silica gel chromatography (0% to 50% EtOAc/hexanes) to afford methyl 2-chloro-3-methyl-4-oxo-3,4-dihydroquinazoline-7-carboxylate (0.12 g, 23%). LC-MS: (FA) ES+ 253; 1H NMR (400 MHz, CDCl3) δ 8.31 (d, J=8.4 Hz, 1H), 8.31 (d, J=1.5 Hz, 1H), 8.10 (dd, J=8.4, 1.5 Hz, 1H), 3.98 (s, 3H), 3.78 (s, 3H).

Provenance & Evidence