(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amine → HCID 22609718, compound

Participants

Reaction Steps

The (4-benzyloxy-phenyl)-(6-bromoquinazolin-4-yl)amine (200 mg, 0.49 mmol), 2-(tributylstannyl)pyrimidine (200 mg, 0.54 mmol) and bis(triphenylphosphine)palladium(II) chloride (catalytic) were dissolved in dioxan (3 ml) and heated at reflux under nitrogen for 27 hr (Procedure B). The solvent was removed from the cooled reaction under vacuum, and the residue was purified by flash column chromatography (silica gel, eluting with an ethyl acetate/iso-hexane gradient). The resulting oily solid was triturated with iso-hexane/ethyl acetate to give the product (80 mg, 40%) as a pale yellow solid; δH [2H6]-DMSO 10.30 (1H, b, NH), 9.61 (1H, s, 5-H), 9.07 (2H, d, pyrimidine 4-H, pyrimidine 6-H), 8.86 (1H, d, 7-H), 8.51 (1H, s, 2-H), 7.93 (1H, d, 8-H), 7.78 (2H, d, 2′-H, 6′-H), 7.65-7.36 (6H, m, 5×Ph-H, pyrimidine 5-H), 7.11 (2H, d, 3′-H, 5′-H), 5.18 (2H, s, CH2); m/z 406 (M+1)+.

Provenance & Evidence