Formic Acid → Adenine

HRID 2294522Notes

Reaction equation

HRID 2294522 reaction equation
[NH2:1][C:2]1[C:7]([N:8]=O)=[C:6]([NH2:10])[N:5]=[CH:4][N:3]=1.[CH:11]([O-])=O.[Na+].C(O)=O.O>C(N)=O.[Pd]>[N:5]1[C:6]([NH2:10])=[C:7]2[C:2]([N:1]=[CH:11][NH:8]2)=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 2597525-Nitroso-4,6-pyrimidinediamineHCID 2723810Sodium Formate

Product 1

HCID 190AdenineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 713FormamideSolvent

Procedure

13.9 g (0.1 mol) 4,6-diamino-5-nitrosopyrimidine was suspended in 50 ml formamide, 6.8 g (0.1 mol) sodium formate, 27.0 g (0.5 mol) 85% formic acid and 0.5 g palladium catalyst were added according to example 1 and the mixture was heated for 4 hours to 110° C. The decolorized suspension was subsequently heated for 3 hours to 180° C. and then cooled. In order to improve the processing, 50 ml water was added and the solid was filtered. The filter cake was dissolved in 160 ml 5% sodium hydroxide solution and the insoluble Pd catalyst was separated. The clear filtrate was adjusted with sulphuric acid to a pH value of 8.5 after a 30 minute treatment at 50° C. with 3 g active carbon. In this process a colorless precipitate separated out from adenine which was suction filtered, washed twice with 30 ml water and dried in a vacuum at 80° C. 12.2 g adenine (0.090 mol, 90% of theory) was obtained in this way as a white powder.

Workup

  1. temperaturethe mixture was heated for 4 hours to 110° C
  2. temperatureThe decolorized suspension was subsequently heated for 3 hours to 180° C.
  3. temperaturecooled
  4. additionwas added
  5. filtrationthe solid was filtered
  6. dissolutionThe filter cake was dissolved in 160 ml 5% sodium hydroxide solution
  7. customthe insoluble Pd catalyst was separated
  8. customat 50° C.
  9. customIn this process a colorless precipitate separated out from adenine which
  10. filtrationfiltered
  11. washwashed twice with 30 ml water
  12. customdried in a vacuum at 80° C

Sources & evidence

ORD record
ord-6ca92aea4b424904b29b5ab7c0d216bd
Source dataset
uspto-grants-1997_11
Patent number
US05688947

Reaction notes

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