Boron tribromide → HCID 136140058, compound

Participants

Reaction Steps

An aryl methoxy derivative p-tolyl-[2-(3,4,5-trimethoxy-phenyl)-quinazolin-4-yl]-amine (2, 30 mg, 7.5e-5 mol) was dissolved in anhydrous DCM (minimal volume, not fully dissolved); the round flask was then sealed. BBr3 (76 μl, 0.111 gr, 205 gr/mol, d=1.45, 2 equiv/per methoxy group, here 6 eq. were used 5.5e-4 mol) was added drop wise (from a syringe) and the reaction mixture was stirred at room temperature for 1 h. The degree of conversion was monitored by HPLC until full conversion was achieved, and the reaction was then quenched with methanol and evaporated to low volume. Another wash was performed using methanol, followed by a wash with acetonitrile and evaporation, to obtain 5-(4-(p-tolylamino)quinazolin-2-yl)benzene-1,2,3-triol, 21 (24 mg, 6.6e-5 mol, 90%). m.p>250° C.; 1H NMR (300 MHz, DMSO-d6) δ 2.35 (s, 3H), 6.75 (s, 2H), 7.22 (d, J=8.0 Hz, 2H), 7.35 (d, J=7.5 Hz, 2H), 7.56 (t, J=8.0 Hz, H), 7.82 (t, J=8.2 Hz, 2H), 8.24 (d, J=7.5 Hz, 1H). Anal. (C21H17N3O3) C, H, N.

Provenance & Evidence