HCID 178515562, compound → HCID 178515560, compound

HRID 1161683Notes

Reaction equation

HRID 1161683 reaction equation
S[C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1>[Ni].N>[C:9]1([C:4]2[N:3]=[CH:2][N:7]=[C:6]([OH:8])[CH:5]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 178515562HCID 178515562, compound

Product 1

HCID 178515560HCID 178515560, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

6-Phenyl-pyrimidin-4-ol was prepared by reducing 2-mercapto-6-phenyl-pyrimidin-4-ol (1.5 g, 7.3 mmol) in the presence of raney nickel (5 equivalents) in aqueous ammonia (30 mL) at room temperature followed by refluxing for 3 hours. The mixture was filtered through Celite™ and extracted with ethyl acetate (3×20 mL). Combined organic layers were dried over anhydrous Na2SO4, concentrated under vacuum and the residue purified by column chromatography to give the desired compound (0.5 g, 40% yield) as a off white solid.

Workup

  1. custom6-Phenyl-pyrimidin-4-ol was prepared
  2. customat room temperature
  3. temperatureby refluxing for 3 hours
  4. filtrationThe mixture was filtered through Celite™
  5. extractionextracted with ethyl acetate (3×20 mL)
  6. dry with materialCombined organic layers were dried over anhydrous Na2SO4
  7. concentrationconcentrated under vacuum
  8. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-ed8e89a9a90540f3b800a9f9445993c8
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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