Formic Acid → Guanine

HRID 2294521Notes

Reaction equation

HRID 2294521 reaction equation
O.[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[C:5]([OH:10])[N:4]=1.N([O-])=O.[Na+].C(O)=O.[CH:18]([NH2:20])=O>[Pd]>[NH:4]1[C:5](=[O:10])[C:6]2[NH:20][CH:18]=[N:9][C:7]=2[N:8]=[C:3]1[NH2:2]

Participants

6

Reactant 4

HCID 284Formic Acid2×HCID 713FormamideHCID 23668193Sodium NitriteHCID 178507953HCID 178507953, compound

Product 1

HCID 135398634Guanine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
80 °C

Procedure

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.

Workup

  1. customthe pink-coloured suspension obtained
  2. temperaturewas heated for 3 hours to 120° C
  3. temperaturewas subsequently heated for 3 hours to 180° C.
  4. customwhile removing a small amount of water
  5. distillationby distillation
  6. addition100 ml water was added
  7. filtrationfiltered
  8. washThe filter cake was washed twice with 50 ml water
  9. dissolutiondissolved in 320 ml of a 5% sodium hydroxide solution
  10. customThe insoluble noble metal catalyst was removed by filtration
  11. customAfter separating the active carbon, guanine
  12. customwas precipitated by addition of 20% sulphuric acid to pH 9.0, suction
  13. filtrationfiltered
  14. washwashed twice with 50 ml water
  15. customdried in a vacuum at 80° C

Sources & evidence

ORD record
ord-bc28d897ff09469ba7b4e5d0678e5842
Source dataset
uspto-grants-1997_11
Patent number
US05688947

Reaction notes

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