N,N-Diethylaniline → HCID 178434331, compound

Participants

Reaction Steps

A mixture of 3-methyl-7-hydroxypyrazolo[4,3-d]pyrimidine (1.0 g, 6.6 mmol), N,N-diethylaniline (2.0 g) and phosphorous oxychloride (16.5 g) was heated with magnetic stirring in an oil bath. The temperature was raised from 55° to 78° over the course of 40 min. At this point, all of the starting material had dissolved and the solution had turned red. The excess POCl3 was distilled off in vacuo (this procedure took 15 min.) and ice-water (50 ml) was added to the residue. The resulting red solution was saturated with sodium chloride (12 g) whereupon it turned yellow. The solution was extracted with ethyl acetate (4×40 ml) and the combined extract was filtered through alumina (5 g; 80-325 mesh), washed with brine (40 ml), dried (Na2SO4) and evaporated, yielding 0.83 g (74%) of eggshell colored crystals.

Provenance & Evidence