Water → 8-(2-Methoxy-4-hydroxy-phenyl)-3H-purin-2-one

HRID 3871Notes

Reaction equation

HRID 3871 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9]CC2C=CC=CC=2)[CH:6]=[CH:5][C:4]=1[C:17]1[NH:25][C:24]2[C:19](=[N:20][C:21]([O:26]CC3C=CC=CC=3)=[N:22][CH:23]=2)[N:18]=1.[H][H].[OH-].[Na+].O>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:17]1[NH:25][C:24]2[CH:23]=[N:22][C:21](=[O:26])[NH:20][C:19]=2[N:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 135323998-(2-Methoxy-4-benzyloxy-phenyl)-2-benzyloxypurineHCID 178418361HCID 178418361, compound

Product 1

HCID 1363937228-(2-Methoxy-4-hydroxy-phenyl)-3H-purin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Three grams of 8-(2-methoxy-4-benzyloxy-phenyl)-2-benzyloxypurine are dissolved in 100 ml of ethanol and hydrogenated in the presence of 1 gm of 20% palladium/charcoal for two hours at 50° C. with hydrogen at 5 bar. The catalyst is filtered off and washed with hot ethanol. The filtrates are evaporated, and the residue is triturated with methylene chloride. The solid product obtained is stirred with 30 ml of 2N sodium hydroxide solution. The solution is filtered, and the filtrate is acidified with glacial acetic acid. The precipitate formed is separated from the solution by centrifuging and purified by triturating with acetone. The product contains 1 mol of water of crystallization.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with hot ethanol
  3. customThe filtrates are evaporated
  4. customthe residue is triturated with methylene chloride
  5. customThe solid product obtained
  6. filtrationThe solution is filtered
  7. customThe precipitate formed
  8. customis separated from the solution by centrifuging
  9. custompurified
  10. customby triturating with acetone

Sources & evidence

ORD record
ord-31404deb6e244db4997f5de822a83ec7
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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