N,N-Diethylaniline → 4-Chloro-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

Add 14.5 ml (13.6 g, 90.8 mmol) N,N-diethylaniline to a suspension of 10.0 g (41.3 mmol) 5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4(3H)-one in 250 ml toluene and heat to 100° C. At this temperature, add 4.2 ml (7.0 g, 45.4 mmol) phosphoryl chloride dropwise, and stir the reaction mixture for 15 h at 100° C. Then add a further 1.2 ml (2.0 g, 13 mmol) phosphoryl chloride and stir the reaction mixture again for 22 h at 100° C. After cooling to room temperature, quickly wash the reaction solution with, successively, 250 ml ice water, twice with 250 ml cold 20% sodium hydroxide solution each time, again with 250 ml ice water, 250 ml satd. sodium chloride solution, 1 N hydrochloric acid and 250 ml ice water. Dry the organic phase over sodium sulphate, filter and concentrate by vacuum evaporation. 6.3 g (59% of theor.) of the title compound is obtained.

Provenance & Evidence