Phenol → 4-phenoxy-6-(1H-pyrazol-1-yl)pyrimidine

HRID 231804Notes

Reaction equation

HRID 231804 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:3]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1>[O:19]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 106312394-Chloro-6-(1H-pyrazol-1-yl)pyrimidine

Product 1

HCID 6613904-phenoxy-6-(1H-pyrazol-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 10 ml of benzene, 180 mg of 6-chloro-4-(1-pyrazolyl)pyrimidine, 175 ml of phenol, and 152 mg of 1,8-diazabicyclo-(5,4,0)-7-undecene (DBU) were dissolved, and refluxed for 7 hours. This reaction solution was washed with water, and an organic fraction was dried over anhydrous sodium sulfate. The resulting extract was distilled to give a residue, and the residue was purified by alumina gel column chromatography using a mixture of n-hexane and ethyl acetate (2:1) to yield 175 mg 6-phenoxy-4-(1-pyrazolyl)pyrimidine, recrystallized from n-hexane, to give an acicular crystal having a melting point of 92.5°-93.5° C.,

Workup

  1. temperaturerefluxed for 7 hours
  2. washThis reaction solution was washed with water
  3. dry with materialan organic fraction was dried over anhydrous sodium sulfate
  4. extractionThe resulting extract
  5. distillationwas distilled
  6. customto give a residue
  7. customthe residue was purified by alumina gel column chromatography
  8. additiona mixture of n-hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-94235ced8b11461db88210b2fadce5e9
Source dataset
uspto-grants-1989_07
Patent number
US04849424

Reaction notes

Loading…