Sodium Carbonate → 5-(4-Hydroxy-6-quinazolinyl)furan-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a 40° C. solution of Na2CO3 (3.9 g, 36 mmol) in inert gas (nitrogen or argon) degassed aqueous dioxane (100 mL, 2:1 dioxane: H2O) was added [HP(t-Bu)3]BF4 (0.52 g, 1.8 mmol) and Pd(OAc)2 (0.4 g, 0.18 mmol). The mixture was stirred at 30° C. (internal temperature) under an atmosphere nitrogen for 30 min, and then 6-iodoquinazolin-4(3H)-one ((Va); 5 g, 18 mmol) and 5-formylfuran-2-ylboronic acid ((VIa); 4.1 g, 29 mmol) were added. The mixture was heated to 80° C. (internal temperature) and stirred until TLC analysis showed completion of the reaction. The reaction product mixture was cooled to ambient temperature and filtered through celite (1 g), and the filter cake was washed with n-BuOH (200 mL). The combined filtrates were separated and the organic layer was washed twice with a saturated aqueous solution of NaCl (100 mL each). The organic phase was concentrated down to about 50 mL under vacuum and the residue was cooled to ambient temperature with stirring to precipitate the product. The slurry was filtered and the filter cake was washed with n-BuOH (40 mL) and then dried at 60° C. under vacuum to give crude compound of formula (IX) (4.5 g, 91% HPLC, 16.5 mmol). 1H NMR (300 MHz, d6-DMSO, 1347-126-19): δ 7.47 (d, J=3.6 Hz, 1H), 7.68 (d, J=3.6 Hz, 1H), 7.77 (d, J=8.7 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H), 8.28 (dd, J=8.7 Hz, J=2.1 Hz, 1H), 8.53 (d, J=2.1 Hz, 1H), 9.64 (s, 1H).

Provenance & Evidence