N-Methyl-4-anisidine → (2-Chloro-6-nitroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine

Participants

Reaction Steps

A mixture of 1.65 g (6.76 mmol) of 2,4-dichloro-6-nitro-quinazoline, 1.02 g (7.44 mmol) of (4-methoxy-phenyl)-methyl-amine, 0.6 g (7.43 mmol) of NaOAc in 6 mL of THF and 6 mL of water was stirred at ambient temperature for 18 hours. The reaction mixture extracted with EtOAc (2×15 mL) and organics were washed with NaHCO3, dried and concentrated. Isolation done by MPLC (0-30% EtOAc/hexanes as eluent) to give 1.86 g of the title compound. 1H NMR (DMSO-d6) δ 8.38-7.13 (7H), 3.84 (s, 3H), 3.59 (s, 3H); LC-MS (ESI+; 345 ([M+H]+)).

Provenance & Evidence