Reaction #3751

Reaction equation

1,3-di-n-propyl-5-nitroso-6-aminouracil

ammonium hydroxide

sodium dithionite

→

1,3-di-n-propyl-5,6-diaminouracil

Yield 64.3%

Solvents

water

Conditions

Workup

1. 1
   ExtractionThe aqueous mixture was extracted with chloroform (8×200 ml)
2. 2
   Dryingdried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified by flash chromatography (5/10% methanol/chloroform)
6. 6
   Otherrecrystallized from 10% isopropanol in hexane
7. 7
   Otherrecrystallized from 10% isopropanol

Procedure

The 1,3-di-n-propyl-5-nitroso-6-aminouracil (61.6 g) was suspended in 1 L of water, and the suspension was made alkaline to pH 11 with 50% ammonium hydroxide and treated with 100 g of sodium dithionite, in portions, until the purple color faded. The aqueous mixture was extracted with chloroform (8×200 ml), dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (5/10% methanol/chloroform) and recrystallized from 10% isopropanol in hexane and recrystallized from 10% isopropanol to yield 37.29 g of 1,3-di-n-propyl-5,6-diaminouracil, m.p., 127°-128° C.

Source