Potassium Carbonate → HCID 68516669, compound

Participants

Reaction Conditions

Reaction Steps

2-{4-[(3,5-Dichloro-4-methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-isoindole-1,3-dione: A mixture of (2-chloromethyl-quinazolin-4-yl)-(3,5-dichloro-4-methoxy-phenyl)-methyl-amine hydrochloride (521 mg, 1.24 mmol), K2CO3 (401 mg, 2.90 mmol) and potassium phthalimide (312 mg, 1.68 mmol) in DMF (7 mL) was heated at 50° C. for 4 h. EtOAc and DCM were added and this was washed with water then 50% satd NaCl then satd NaCl. The organic layer was dried (MgSO4), filtered through a pad of silica with an EtOAc wash then most of the solvents were removed on a rotary evaporator. The remaining solvent was removed from the crystalline material that had formed and the product was washed with two portions of EtOAc then suspended in hexanes, collected by filtration and washed with hexanes. The title compound was obtained as a paleyellow microcrystalline solid (373 mg; 61%). 1H NMR (CDCl3) δ 7.96-7.91 (m, 2H), 7.79-7.40 (m, 3H), 7.60 (m, 1H), 7.16-7.06 (m, 2H), 7.04 (s, 2H), 5.16 (s, 2H), 3.90 (s, 3H), 3.30 (s, 3H); LC-MS (ESI+; 493 ([M+H]+)).

Provenance & Evidence