Diisopropylethylamine → N2-(2-amino-ethyl)-N4-(3,4-dimethoxy-phenyl)-N4-methyl-quinazoline-2,4-diamine

Participants

Reaction Steps

(2-{4-[(3,4-Dimethoxy-phenyl)-methyl-amino]-quinazolin-2-ylamino}-ethyl)-carbamic acid tert-butyl ester: A soln of (2-chloro-quinazolin-4-yl)-(3,4-dimethoxy-phenyl)-methyl-amine (440 mg, 1.33 mmol), ethyl-diisopropyl-amine (0.47 mL, 2.70 mmol) and (2-amino-ethyl)-carbamic acid tert-butyl ester (316 μL, 2.00 mmol) in n-BuOH (5 mL) was reacted at 110° C. for 29 h then concd on a rotary evaporator. The crude material was dissolved in CHCl3 (8 mL) then washed with satd NaHCO3 (2×3 mL) and water (1×3 mL). This soln was dried (MgSO4), filtered through a plug of silica with a wash of 100:10:1 CHCl3:MeOH:concd NH4OH, concentrated, then purified by MPLC (amine column (Isco 68-2203-101)/0-100% i-PrOH in CHCl3.), yielding the title compound as a tan solid (550 mg; 91%). 1H NMR (CDCl3) δ 7.46-7.35 (m, 2H), 6.90-6.82 (m, 2H), 6.77-6.66 (m, 3H), 5.80 (s(br), 1H), 5.44 (s(br), 1H), 3.92 (s, 3H), 3.79 (s, 3H), 3.68 (m, 2H), 3.53 (s, 3H), 3.44 (m, 2H), 1.44 (s, 9H); LC-MS (ESI+; 454 ([M+H]+)).

Provenance & Evidence