Water → HCID 15346448, compound

Participants

Reaction Steps

2.16 g (9 mmol) of 5-chloro-6-ethyl-4-(1,3-dihydroxy-2-propylamino)-pyrimidine (Example 1), 1.80 g (18 mmol) of 2-hexanone and 500 mg of p-toluenesulfonic acid were heated in 100 ml of toluene for 8 hours, using a water separator. After the mixture had been extracted by stirring with dilute sodium hydroxide solution, the organic phase was dried and concentrated. The cis/trans isomers were separated by chromatography over silica gel (mobile phase: ethyl acetate/petroleum ether 4:1). 0.29 g of trans isomer (10.3% of theory, colorless oil) was first eluted, followed by 0.49 g of the cis isomer (17.3% of theory, colorless oil).

Provenance & Evidence