Benzyl Bromide → 2-[N-(3-aminopropyl)-N-benzylamino)pyridine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of sodium hydride (0.7 g) and 2-(3-aminopropylamino)pyridine (4.02 g) in DMSO (25 ml) was heated slowly to 75° C. under nitrogen. After the evolution of hydrogen had ceased the solution was cooled to room temperature and benzyl bromide (3.17 ml) added dropwise below 35° C. After a further 30 minutes water was added and the mixture extracted with chloroform. The chloroform extracts were washed with 2N hydrochloric acid, the pH of the aqueous layers ajusted to 4.5 and re-extracted with chloroform. The pH was further raised to 14 and again extracted with chloroform. After drying (K2CO3), the final chloroform extract, on stripping, afforded 2-[N-(3-aminopropyl)-N-benzylamino]pyridine as an oil (3.91 g) which was used without further purification. (ii) 2-[N-(3-aminopropyl)-N-benzylamino]pyridine (1.64 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (1.48 g) were heated together under reflux in pyridine (15 ml) for 20 hr. After stripping the residue was treated with wet ether and the resulting solid recrystallised from ethanol/water to give 2-[3-(N-benzyl-N-pyrid-2-ylamino)propylamino]-5-(6-methylpyrid-3-ylmethyl)-pyrimid-4-one 0.75H2O, 1.46 g (56%) mp 90°-96° C.

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