Toluene → n-((5-(4-Chloroquinazolin-6-yl)furan-2-yl)methyl)-2-(methylsulfonyl)ethanamine

Participants

Reaction Steps

In a 4-neck glass flask provided with a mechanical stirrer, condenser and thermometer, the entirety having been previously dried, 63.8 g of 6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl] quinazoline-4-ol of formula (VI) (0.184 moles), 33.7 g (20.1 mL) of phosphoryl oxychloride (POCl3; 0.220 moles) and 150 mL of toluene were introduced, under nitrogen. Stirring was carried out at ambient temperature for 10 minutes then 22.3 g (30.7 mL) of triethylamine (0.220 moles) was dosed, maintaining the T below 30° C. After introduction heating was carried out at 75° C. for 3 hours. The reaction was controlled by means of TLC using the Hexane/Ethyl acetate mixture (4:6) as eluent. Cooling was carried out at 0° C. and stirring was carried out for an hour at such temperature. The suspension was filtered washing the solid with 100 mL of toluene. The product was dried at 50° C. for 7-8 hours under vacuum. 63.8 g of product was added with a molar yield equivalent to 95%.

Provenance & Evidence