N,N-Diethylaniline → HCID 67282040, compound

Participants

Reaction Conditions

Reaction Steps

Into a round bottom flask was added methyl 3-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-6-carboxylate (1.3 g, 5.3 mmol) dissolved in phosphoryl chloride (20.0 mL, 214 mmol). N,N-diethylaniline (2.6 mL, 16.0 mmol) was added followed by phosphorus pentachloride (0.56 g, 2.7 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-6-carboxylate (0.36 g, 26%). LC-MS: (FA) ES+ 253; 1H NMR (400 MHz, CDCl3) δ 8.92 (d, J=2.0 Hz, 1H), 8.38 (dd, J=8.5, 2.0 Hz, 1H), 7.67 (d, J=8.5 Hz, 1H), 3.97 (s, 3H), 3.78 (s, 3H).

Provenance & Evidence