Xanthine → Hypoxanthine

HRID 2227358Notes

Reaction equation

HRID 2227358 reaction equation
[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[NH:4][C:2]1=O>C(O)CC.[Ni]>[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[CH:2]1

Participants

4

Reactant 1

HCID 1188Xanthine

Product 1

HCID 135398638HypoxanthineYield 70.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 10311-PropanolSolvent

Procedure

2.18 g (4.5 mM) of xanthine (B.) and 2.6 g of Raney-nickel (treated with 0.1% aqueous acetic acid) were refluxed in 30 ml of 1-propanol for 2.5 hr. The nickel was filtered off and the solution evaporated in vacuo to dryness. The residue was dissolved in 40 ml of ethyl acetate and extracted with sodium bicarbonate solution. The formed solid is filtered off and the organic phase evaporated in vacuo to dryness (1.95 g). A dichloromethane solution, comprising 2% of methanol, was purified on 19 g of silicagel in a column. Crystallization from ethyl acetate gave 1.37 g (67.2%) of hypoxanthine with mp 159-161° C., a second crop gave 0.4 g (2.0%) of hypoxanthine.

Workup

  1. filtrationThe nickel was filtered off
  2. customthe solution evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in 40 ml of ethyl acetate
  4. extractionextracted with sodium bicarbonate solution
  5. filtrationThe formed solid is filtered off
  6. customthe organic phase evaporated in vacuo to dryness (1.95 g)
  7. customwas purified on 19 g of silicagel in a column
  8. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-06e5b962ad854af88548cd8d01720c10
Source dataset
uspto-grants-2002_07
Patent number
US06413975B1

Reaction notes

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