Formic Acid → Guanine

Participants

Reaction Conditions

Reaction Steps

29.0 g (0.2 mol) 2,4-diamino-6-hydroxypyrimidine hydrate was nitrosed with 13.8 g (0.2 mol) sodium nitrite and 10.8 g (0.2 mol) 85% formic acid in 150 ml formamide and the pink-coloured suspension obtained was admixed with a further 42.4 g (0.8 mol) 85% formic acid. After stirring in 1.0 g of a palladium catalyst on active carbon according to example 1, it was heated for 3 hours to 120° C. In this process the suspension became colorless and was subsequently heated for 3 hours to 180° C. while removing a small amount of water by distillation. After cooling to 80° C., 100 ml water was added and the solid was suction filtered. The filter cake was washed twice with 50 ml water and dissolved in 320 ml of a 5% sodium hydroxide solution. The insoluble noble metal catalyst was removed by filtration and the filtrate was stirred for 30 minutes at 50° C. with 3 g active carbon. After separating the active carbon, guanine was precipitated by addition of 20% sulphuric acid to pH 9.0, suction filtered, washed twice with 50 ml water and dried in a vacuum at 80° C. 26.7 g (0.174 mol, 87% of theory) 98.4% pure guanine was obtained in this manner.

Provenance & Evidence