Sodium Dithionite → 2-amino-7,7-diethyl-6-(hydroxymethyl)-1,8-dihydropteridin-4-one

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Reaction Steps

Sodium dithionite was added portionwise to a warm solution of 2-amino-4-hydroxy-6-(1,1-diethyl-3-hydroxy-2-hydroxyiminopropylamino)-5-nitropyrimidine (II) (450 mg) in 0.1M sodium hydroxide until the colour changed from red to very pale yellow. A solid product was not obtained either on cooling or on adjusting the pH. In order to separate the product from inorganic material the solution was evaporated and the product extracted with ethanol and the inorganic material was filtered off. This extraction was repeated and the combined extracts were evaporated to dryness in vacuo. The residue was dissolved in the minimum quantity of water and placed on a column of Amberlite (C.G.50) ion exchange resin (2.5 × 28 cm). Elution with water gave two main fluorescent bands. Evaporation of the solution containing the first band gave the 6-carboxaldehyde derivative of the title compound (10 mg, yield 3%) as a bright orange powder, whilst the second band gave the 7,8-dihydropteridine (I) (160 mg, yield 44.5%) as a bright yellow powder, m.p. <300° decomp.

Provenance & Evidence