Sodium Dithionite → 1,3-Diallyl-5,6-diaminouracil

HRID 356877

Reaction equation

HRID 356877 reaction equation
[CH2:1]([N:4]1[C:11]([NH2:12])=[C:10]([N:13]=O)[C:8](=[O:9])[N:7]([CH2:15][CH:16]=[CH2:17])[C:5]1=[O:6])[CH:2]=[CH2:3].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O>[CH2:1]([N:4]1[C:11]([NH2:12])=[C:10]([NH2:13])[C:8](=[O:9])[N:7]([CH2:15][CH:16]=[CH2:17])[C:5]1=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 572531Uracil, 1,3-diallyl-6-amino-5-nitroso-

Product 1

HCID 135250621,3-Diallyl-5,6-diaminouracilYield 104.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 1,3-diallyl-5-nitroso-6-aminouracil (4.5 g) was suspended in 150 ml of ethyl acetate and treated with 23.6 g of sodium dithionite in 64 ml of water. After 1 hour, the layers were separated and the aqueous phase was extracted with ethyl acetate (4×100 ml). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated and the residue was purified by flash chromatography (10% methanol in chloroform) to yield 4.41 g of 1,3-diallyl-5,6-diaminouracil.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (4×100 ml)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography (10% methanol in chloroform)

Sources & evidence

ORD record
ord-5a10bb60524a4263b6c83b543acddf43
Source dataset
uspto-grants-1998_11
Patent number
US05840729

Linked notes

Loading…