HCID 178518408, compound → HCID 178518407, compound

HRID 973774Notes

Reaction equation

HRID 973774 reaction equation
[OH:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7](S)[N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([OH:18])[N:3]=1>[OH-].[Na+].[Ni]>[OH:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([OH:18])[N:3]=1

Participants

4

Reactant 1

HCID 178518408HCID 178518408, compound

Product 1

HCID 178518407HCID 178518407, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

10 g of 2,6-dihydroxy-9-phenyl-8-purinethiol was dissolved in about 100 ml 1N sodium hydroxide followed by addition of about 30 g Raney nickel. Slight foaming occurred. The reaction was slowly heated to reflux (oil bath about 120° C.). After 1.5 hours the reaction was filtered. The filtrate was cooled to about 4° C. and filtered. The white solid was dissolved in hot water treated with charcoal, filtered and treated with concentrated hydrochloric acid to produce a white precipitate. This was filtered, dried under vacuum at 80° C. for three hours to yield 3.3 g of 2,6-dihydroxy-9-phenylpurine (38% yield).

Workup

  1. temperatureThe reaction was slowly heated
  2. filtrationAfter 1.5 hours the reaction was filtered
  3. temperatureThe filtrate was cooled to about 4° C.
  4. filtrationfiltered
  5. dissolutionThe white solid was dissolved in hot water
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. additiontreated with concentrated hydrochloric acid
  9. customto produce a white precipitate
  10. filtrationThis was filtered
  11. customdried under vacuum at 80° C. for three hours

Sources & evidence

ORD record
ord-74beb6dc19ad452dbb93fe982fa2fbb4
Source dataset
uspto-grants-1991_11
Patent number
US05064947

Reaction notes

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