HCID 178515562, compound → HCID 178515560, compound

HRID 1836105Notes

Reaction equation

HRID 1836105 reaction equation
S[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[C:4]([OH:14])[N:3]=1>[Ni].N>[OH:14][C:4]1[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=[CH:2][N:3]=1

Participants

4

Reactant 1

HCID 178515562HCID 178515562, compound

Product 1

HCID 178515560HCID 178515560, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

To 2-mercapto-6-hydroxy-4-phenylpyrimidine (10 g) in ‘880’ ammonia solution (100 ml) was carefully added Raney nickel (32.5 g, 50% slurry) portionvise. Immediate effervescence took place. The mixture was heated to reflux for 4 hours, filtered and concentrated under reduced pressure. The initial residue was azeotroped with toluene (×2) to remove final traces of water. The pale blue residue was dissolved in hot ethanol and filtered and then the filtrate was treated with charcoal. The resulting green solution was evaporated under reduced pressure to afford crude 4-hydroxy-6-phenylpyrimidine (4.65 g) as a green solid (m.p.>300° C.) which was used in the next stage without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe initial residue was azeotroped with toluene (×2)
  6. customto remove final traces of water
  7. dissolutionThe pale blue residue was dissolved in hot ethanol
  8. filtrationfiltered
  9. additionthe filtrate was treated with charcoal
  10. customThe resulting green solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f89586856c0f48a8bb216ae13feeac11
Source dataset
uspto-grants-2004_08
Patent number
US06777412B2

Reaction notes

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