N,N-Dimethylaniline → HCID 86732869, compound

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Reaction Steps

2.4 G. of N,N-dimethyl-aniline were added dropwise with stirring to a suspension of 3.4 g. of α-(2,4-diamino-6-hydroxy-5-pyrimidinyl)-2,6-dimethoxy-p-toluic acid methyl ester in 25.6 g. of phosphorus oxychloride. The resulting mixture was brought to the boiling temperature in the course of 1 hour and then boiled at reflux for 4 hours. Thereafter, two thirds of the phosphorus oxychloride were removed by distillation under reduced pressure. The residue was poured onto 80 g. of ice with stirring and left to stand for two days at room temperature. The suspension was treated with 38 ml. of 25% aqueous ammonia, while the temperature did not exceed 20°C. After 2 hours, the solid material was removed by filtration with suction, rinsed with a small amount of water in a flask and separated from the N,N-dimethyl-aniline with steam. After cooling, the compound in suspension was removed by filtration with suction and taken up in ethyl acetate. The solution was dried over magnesium sulfate and the solvent evaporated. The dark residue (1.6 g.) was purified by column chromatography on 60 g. of silica gel (Merck) using chloroform/n-propanol/25% ammonia (80:20:1) as the eluant, whereby there was obtained α-(2,4-diamino-6-chloro-5-pyrimidinyl)-2,6-dimethoxy-p-toluic acid methyl ester having a m.p. of 228°-229°C. (from methanol).

Provenance & Evidence