Water → N~1~-[(3-Chlorophenyl)methyl]-N~1~-(pyridin-2-yl)propane-1,3-diamine

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Reaction Steps

Sodium hydride (1.32 g) was dissolved in DMSO (25 ml) at 70°-75° C. under nitrogen. The solution was cooled and 2-(3-aminopropylamino)pyridine (7.56 g) in DMSO (20 ml) added at room temperature. 3-Chlorobenzyl chloride (8.86 g) in DMSO (15 ml) was added dropwise maintaining the temperature at 20°-25° C. After a further 1 hour, water was added (200 ml) and the mixture extracted with ether. The ether extracts were washed with 2N hydrochloric acid and the aqueous layer adjusted to pH 3.5. After extracting with chloroform the pH was raised to 14 and extracted with ether. After drying (K2CO3), the final ether extracts were stripped to give 2-[N-(3-aminopropyl)-N-(3-chlorobenzyl) amino]pyridine (8.34 g) as an oil which was used without further purification. (ii) 2-[N-(3-aminopropyl)-N-(3-chlorobenzyl)amino]pyridine (1.65 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (1.3 g) were heated together under reflux in pyridine (15 ml) for 20 hr. On cooling, the mixture was stripped, the residue triturated with wet ether and recrystallised twice from ethanol/water to give 2-[3-[N-(3-chlorobenzyl)-N-pyrid-2-ylamino]propylamino]-5-(6-methylpyrid-3-ylmethyl) pyrimid-4-one 0.6H2O, 1.29 g (53%) mp 100°-104° C.

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