Methanol → Hypoxanthine

HRID 1976560Notes

Reaction equation

HRID 1976560 reaction equation
C(OC1C=C(C=CC=1OC)C[N:13]1[C:21]2[N:20]=[C:19](C(OCC3C=CC=CC=3)(C)C)[NH:18][C:17]=2[C:16](=[O:33])[NH:15][C:14]1=S)C1C=CC=CC=1.C(OC1C=C(C=CC=1OC)CN1C2N=C(C(OCC3C=CC=CC=3)(C)C)NC=2C(=O)N=C1)C1C=CC=CC=1.CO>C(O)CC.[Ni]>[NH:15]1[C:16](=[O:33])[C:17]2[NH:18][CH:19]=[N:20][C:21]=2[N:13]=[CH:14]1

Participants

6

Reactant 3

HCID 887MethanolHCID 9914306HCID 9914306, compoundHCID 21998625HCID 21998625, compound

Product 1

HCID 135398638HypoxanthineYield 35.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 10311-PropanolSolvent

Procedure

3-(3-Benzyloxy-4-methoxy-benzyl)-8-(1-benzyloxy-1-methyl-ethyl)-2-thioxanthine (26.05 g, 48 mmole) was heated under reflux in 1-propanol (700 ml) with Raney-nickel (29 g) (treated with 0.1% aqueous acetic acid) for 1.5 hours. The nickel was filtered off and the solvent evaporated in vacuo. The residue was dissolved in dichloromethane (300 ml), extracted with sodium carbonate solution and evaporated again to dryness. The residue was dissolved in methanol (150 ml), treated with charcoal, filtered, concentrated and crystallized to give 3-(3-benzyloxy-4-methoxy-benzyl)-8-(1-benzyloxy-1-methyl-ethyl)-hypoxanthine (15.81 g, 64.5%), mp 78-86° C. (containing methanol). A second crop gave 2.29 g (9.3%) of hypoxanthine.

Workup

  1. filtrationThe nickel was filtered off
  2. customthe solvent evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (300 ml)
  4. extractionextracted with sodium carbonate solution
  5. customevaporated again to dryness
  6. dissolutionThe residue was dissolved in methanol (150 ml)
  7. additiontreated with charcoal
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customcrystallized
  11. customto give

Sources & evidence

ORD record
ord-5e4d8350c5b64a86a59dbb3ab0e03367
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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