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

HRID 1658248Notes

Reaction equation

HRID 1658248 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]([N+]([O-])=O)=[C:12]([NH:20][C:21]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:22](=[N:25]O)[CH2:23][OH:24])[N:11]=1>[OH-].[Na+]>[NH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]2[N:25]=[C:22]([CH2:23][OH:24])[C:21]([CH2:29][CH3:30])([CH2:27][CH3:28])[NH:20][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 178446283HCID 178446283, compound

Product 1

HCID 1784367582-amino-7,7-diethyl-6-(hydroxymethyl)-1,8-dihydropteridin-4-oneYield 3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

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.

Workup

  1. customA solid product was not obtained
  2. temperatureon cooling
  3. customIn order to separate the product from inorganic material the solution
  4. customwas evaporated
  5. extractionthe product extracted with ethanol
  6. filtrationthe inorganic material was filtered off
  7. extractionThis extraction
  8. customthe combined extracts were evaporated to dryness in vacuo
  9. dissolutionThe residue was dissolved in the minimum quantity of water
  10. washElution with water
  11. customgave two main fluorescent bands
  12. customEvaporation of the solution
  13. additioncontaining the first band

Sources & evidence

ORD record
ord-5ca4ae4375704e34a1b8035f32fc74c1
Source dataset
uspto-grants-1976_06
Patent number
US03963719

Reaction notes

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