Water → 2-[N-(3-aminopropyl)-N-propylamino]pyridine

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (1.14 g) was dissolved in DMSO (20 ml) at 70°-75° C. The solution was cooled and 2-(3-aminopropylamino)pyridine (6.57 g) in DMSO (20 ml) added at room temperature. n-Propyl iodide (8.13 g) in DMSO (10 ml) was added dropwise maintaining the temperature at 20-25° C. After standing overnight, water (250 ml) was added and the mixture extracted with ether. The ether extracts were washed with 2N hydrochloric acid and the aqueous layers basified to pH 10.5. After extracting with ether and chloroform the pH was raised to 14 and again extracted with ether. After drying (K2CO3), the final ether extract, on stripping, afforded 2-[N-(3-aminopropyl)-N-propylamino]pyridine (3.4 g) as an oil which was used without further purification. (ii) 2-[N-(3-aminopropyl)-N-propylamino]pyridine (1.74 g) and 2-methylthio-5-(4-chlorobenzyl)pyrimid-4-one (1.6 g) were fused together on an oil bath at 160° C. for 2 hr. On cooling the residue was crystallised three times from ethanol to give 2-[3(N-propyl-N-pyrid-2-ylamino)propylamino]-5-(4-chlorobenzyl)pyrimid-4-one 1.1H2O, 0.8 g (31%) mp 120°-28° C. (softens).

Provenance & Evidence