Ethanol → HCID 15136447, compound

Participants

Reaction Steps

A mixture of N,N'-bis(1H-indol-1-yl)-5-nitro-4,6-pyrimidinediamine (4 g, 10.4 mmole) in 250 ml ethanol containing 200 mg PtO2 was hydrogenated at 55 psi for four hours, then was filtered and evaporated to 4 g of a solid, m.p. 198°-200° C. A solution of 4-[N-(1H-indol-1-yl)-6-[N-(1H -indol-1-yl)]-4,5,6-pyrimidinetriamine (6 g, 17 mmole) in 25 ml triethyl orthoformate and 9 ml glacial acetic acid stirred one hour at 90° C. then was cooled and evaporated. The residue was dissolved in ether and washed with water, sodium carbonate solution, again with water and saturated sodium chloride, then was dried (anhydrous MgSO4), filtered and evaporated to 6 g of an oil. This oil was purified by flash chromatography to give 4 g of a solid. This solid was recrystallized twice from ethyl acetate-petroleum ether to give 2.8 g (49% overall) of 9-(1H-indol-1-yl)-N-(1H-indol-9H-purin-6-amine, m.p. 196°-198° C.

Provenance & Evidence