4-Chloro-6,7-bis(2-methoxyethoxy)quinazoline → HCID 71503222, compound

Participants

Reaction Steps

4-Chloro-6,7-bis(2-methoxyethoxy)quinazoline (140 mg, 0.447 mmol) and 5-ethynyl-2-fluoroaniline (66 mg, 0.489 mmol) were reacted in refluxing isopropanol (3 mL) overnight under an atmosphere of N2. The solvent was removed by rotary evaporation and the residue was dissolved in CHCl3 and then treated with saturated aqueous NaHCO3. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was chromatographed on silica using 40% acetone/CH2Cl2 to provide 116 mg of the pure title product as its free base. This oil was dissolved in a minimum volume of CHCl3, diluted with several volumes of ether and titrated with 1M HCl in ether to precipitate the title product as a white solid (99 mg; 54%; LC-MS: m/z=412.1664, m/z(calc)=412.1667).

Provenance & Evidence