Benzyl Bromide → HCID 20262870, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (0.83 g) in DMSO (25 ml) was added 2-(3-aminopropylamino)-5-bromopyridine (4.6 g). The mixture was stirred and heated slowly, to 85° C. After the evolution of hydrogen had ceased the mixture was cooled to room temperature and benzyl bromide (3.42 g) in DMSO (5 ml) added dropwise maintaining the temperature below 30° C. After standing overnight, water was added and the mixture extracted with ether. The ether extract was washed with 2N hydrochloric acid. The pH of the acid extract was raised to 2.5 (NaOH) and extracted with chloroform. The pH was raised further to 14 and again extracted with chloroform. After drying (K2CO3), the final extract was stripped to give 2-[N-(3-aminopropyl)-N-benzylamino]-5-bromopyridine (4.6 g) as an oil which was used without further purification. (ii) 2-[N-(3-aminopropyl)-N-benzylamino]-5-bromopyridine (1.97 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (1.34 g) were heated together under reflux in pyridine (15 ml) for 20 hr. After stripping, the residue was triturated with ether, recrystallised from methanol and chromatographed (silica gel, 1-2% methanol/chloroform) to give 2-[3-[N-benzyl-N-(5-bromopyrid-2-yl)-amino]propylamino]-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one, 0.2H2O, 1.01 g (38%) mp 150°-55° C. (from ethanol).

Provenance & Evidence