Ethanolamine → HCID 18753227, compound

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.

1. customthe yellow solution was evaporated
2. dissolutionthe residue dissolved in 300 ml dichloromethane
3. washThe organic phase was washed twice with 50 ml of water
4. extractionthe two aqueous phases were re-extracted with 50 ml of dichloromethane
5. dry with materialThe combined organic phases were dried over sodium sulfate
6. customevaporated under reduced pressure
7. customFor purification and separation of the two isomers
8. customthe crude material (3.2 g) was chromatographed (2×) on silica gel using
9. additiona 2:1 mixture of hexane and ethyl acetate as the eluent

ORD record

ord-09ab8af5178b4e539378c63d5a57684f

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06673795B2