HCID 21998633, compound → HCID 9822510, compound

HRID 1976563Notes

Reaction equation

HRID 1976563 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:12][N:13]1[C:21]2[N:20]=[C:19]([CH:22]([CH3:24])[CH3:23])[NH:18][C:17]=2[C:16](=[O:25])[NH:15][C:14]1=S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)CC.[Ni]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:12][N:13]1[C:21]2[N:20]=[C:19]([CH:22]([CH3:24])[CH3:23])[NH:18][C:17]=2[C:16](=[O:25])[N:15]=[CH:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 21998633HCID 21998633, compound

Product 1

HCID 9822510HCID 9822510, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 10311-PropanolSolvent

Procedure

3-(3-Benzyloxy-4-methoxy-benzyl)-8-isopropyl-2-thioxanthine (21.83 g, 50 mmole) was heated under reflux in 1-propanol (700 ml) with Raney-nickel (30 g) (pre-treated with 0.1% of aqueous acetic acid). After 4 hours the nickel was filtered off and washed with hot propanol and chloroform. The solution was evaporated to dryness in vacuo. The residue was dissolved in chloroform, extracted with IM sodium carbonate solution, dried (Na2SO4), treated twice with charcoal (0.8 g), filtered and evaporated to dryness in vacuo. The residue was suspended in hot acetone (250 ml), concentrated and the solid collected at 0-5° C. to give 3-(3-benzyloxy-4-methoxy-benzyl)-8-isopropyl-hypoxanthine (15.27 g, 75.5%), mp 233-235° C.

Workup

  1. filtrationAfter 4 hours the nickel was filtered off
  2. washwashed with hot propanol and chloroform
  3. customThe solution was evaporated to dryness in vacuo
  4. dissolutionThe residue was dissolved in chloroform
  5. extractionextracted with IM sodium carbonate solution
  6. dry with materialdried (Na2SO4)
  7. additiontreated twice with charcoal (0.8 g)
  8. filtrationfiltered
  9. customevaporated to dryness in vacuo
  10. concentrationconcentrated
  11. customthe solid collected at 0-5° C.

Sources & evidence

ORD record
ord-3da6cae8d807459bb8d9d432ca4a3c20
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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