Water → 2-[N-(4-aminobutyl)-N-propylamino]pyridine

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Reaction Steps

Sodium hydride (1.1 g) was disolved in DMSO (20 ml) at 70°-75° C. under nitrogen. The solution was cooled and 2-(4-aminobutylamino)pyridine (6.9 g) in DMSO (20 ml) added at room temperature. n-Propyl iodide (7.81 g) in DMSO (10 ml) was added dropwise maintaining the temperature at 25°-35° C. After a further 15 min water (200 ml) was added and the mixture extracted with ether. The ether extract was washed with 2N hydrochloric acid and the aqueous layer basified to pH 6. After extracting with chloroform, the pH of the aqueous layer was raised to 14 and extracted with ether. The ether extracts were washed with 0.1N sodium hydroxide, dried (K2CO3) and stripped to give 2-[N-(4-aminobutyl)-N-propylamino]pyridine (5.79 g) as an oil which was used without further purification. (ii) 2-[N-(4-aminobutyl)-N-propylamino]pyridine (1.24 g) and 2-methylthio-5-(3,4-methylenedioxybenzyl)pyrimid-4-one (1.38 g) were fused together in an oil bath at 160° C. for 2.5 hr. On cooling the residue was crystallised twice from ethanol/water and finally from acetone/water to give 2-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]-5-(3,4-methylenedioxybenzyl)pyrimid-4-one 1.95H2O, 1.11 g (47%) mp indeterminate.

Provenance & Evidence