Xanthine → Hypoxanthine

HRID 2227357Notes

Reaction equation

HRID 2227357 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 9.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 10311-PropanolSolvent

Procedure

A solution with 22.39 g (43 mM) of the above xanthine (B.) in 580 ml of 1-propanol was treated with 25 g of Raney-nickel (washed with 0.1% aqueous acetic acid) and refluxed for 2 hr. The nickel was filtered off and the solvent evaporated in vacuo. The residue was crystallized from 120 ml of methanol: 12.73 g (60.6%) of hypoxanthine with mp 161-162° C., a second crop gave 1.97 g (9.4%) of hypoxanthine.

Workup

  1. temperaturerefluxed for 2 hr
  2. filtrationThe nickel was filtered off
  3. customthe solvent evaporated in vacuo
  4. customThe residue was crystallized from 120 ml of methanol

Sources & evidence

ORD record
ord-0e4089b943754d1ca8b1bd1c4152bb3d
Source dataset
uspto-grants-2002_07
Patent number
US06413975B1

Reaction notes

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