(1,1'-Biphenyl)-2-ol → HCID 57654588, compound

Participants

Reaction Steps

A solution of 6-iodo-3-(4-methoxy-benzyl)-3H-quinazolin-4-one (0.69 g, 1.75 mmol), malonic acid diethyl ester (0.56 g, 3.49 mmol), copper iodide (0.016 g, 0.090 mmol), biphenyl-2-ol (0.029 g, 0.175 mmol) and cesium carbonate (0.86 g, 2.63 mmol) in THF (10 mL) was heated to 70° C. in a sealed tube for 24 hours. The solution was then cooled to room temperature, saturated sodium bicarbonate was added and the crude product was extracted from ethyl acetate. The product was purified via silica gel column chromatography in hexane:ethyl acetate (1:1) to give 0.51 g (69%) of 2-[3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-malonic acid diethyl ester. 1H NMR (400 MHz, CDCl3) δ 8.21 (m, 1H), 8.05 (s, 1H), 7.80 (dd, 1H, J=2.0, 8.4 Hz), 7.62 (d, 1H, J=8.4 Hz), 7.22 (d, 2H, J=8.8 Hz), 6.78 (d, 2H, J=8.8 Hz), 5.05 (s, 2H), 4.69 (s, 1H), 4.15 (m, 4H), 3.70 (s, 3H), 1.19 (m, 6H).

Provenance & Evidence