Ethanolamine → HCID 18753227, compound

Participants

Reaction Steps

A solution of 3.0 g (14.4 mmol) of 2,4,6-trichloro-5-cyano-pyrimidine (example 38a) and 2.51 ml (14.4 mmol) of N-ethyl-diisopropylamine in 90 ml of dioxane was treated at room temperature with 0.88 ml (14.4 mmol) of ethanolamine and stirred during 18 hours. For the working-up, the yellow solution was evaporated and the residue dissolved in 300 ml dichloromethane. The organic phase was washed twice with 50 ml of water, and the two aqueous phases were re-extracted with 50 ml of dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated under reduced pressure. For purification and separation of the two isomers, the crude material (3.2 g) was chromatographed (2×) on silica gel using a 2:1 mixture of hexane and ethyl acetate as the eluent giving 0.85 g (3.6 mmol, 25% of theory) of the 2,4-dichloro-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile (less polar isomer); MS: [M]+=232; 1.51 g (6.5 mmol, 45% of theory) of the 4,6-dichloro-2-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile (more polar isomer); MS: [M]+=232; and 0.26 g (1.1 mmol, 8% of theory) of a mixture of the two isomers.

Provenance & Evidence