Chloroform → 3-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylamino}-propan-1-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine hydrochloride (88 mg, 0.26 mmol) and 3-amino-propan-1-ol (62 μL, 0.82 mmol) in n-BuOH (2 mL) was heated at 115° C. for 29 h then concd in vacuo. Chloroform (5 mL) was added and this washed with satd NaHCO3 (1×2 mL); then dried (MgSO4), filtered through silica with a wash of 100:10:1 CHCl3:MeOH:concd NH4OH, concd then purified by MPLC (amine column (Isco 60-2203-201)/0-100% i-PrOH in CHCl3) yielding the title compound as a pale yellow oil (70 mg; 79%). 1H NMR (CDCl3) δ 7.43 (m, 1H), 7.38 (m, 1H), 7.12 (m, 2H), 6.92 (m, 2H), 6.80 (m, 1H), 6.69 (m, 1H), 3.84 (s, 3H), 3.78-3.66 (m, 4H), 3.52 (s(br), 3H), 1.81 (m, 2H); LC-MS (ESI+; 339 ([M+H]+)).

Provenance & Evidence