Triethylamine → (4-Benzyloxy-phenyl)-(6-(3-methyl-[1,2]oxazol-4-yl)-quinazolin-4-yl)-amine

Participants

Reaction Steps

(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine hydrochloride (0.35 g) in dioxan (10 ml) under nitrogen was treated with 4-tributylstannyl-3-methylisoxazole (prepapred according to the literature method: Heterocycles, (1996), 43(6), 1301-1304) (0.4 g), silver oxide (0.092 g), triethylamine (0.1 ml) and [1.4-bis(diphenylphosphino)butane]palladium (II) chloride (0.1 g) at 90° C. for 16 hours. The mixture was cooled, adsorbed onto silica and purified by chromatography. Trituration from hexane and filtration gave the title compound (0.20 g); δH [2H6]DMSO 9.78(1H, bs), 9.22(1H, s), 8.57(1H, s), 8.53(1H, s), 7.98(1H, d), 7.83(1H, d), 7.67(2H, d), 7.42(5H, m), 7.09(1H, d), 5.64(2H, s) 2.51 (3H, s); m/z (M+1)+ 409.

Provenance & Evidence