Phosphorus oxychloride → 4-Chloro-2-phenyl-5H-indolo[3,2-d]pyrimidine

HRID 2211221Notes

Reaction equation

HRID 2211221 reaction equation
O[C:2]1[C:3]2[NH:20][C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.P(Cl)(Cl)([Cl:23])=O>O1CCOCC1>[Cl:23][C:2]1[C:3]2[NH:20][C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517456HCID 178517456, compound

Product 1

HCID 152847324-Chloro-2-phenyl-5H-indolo[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-Hydroxy-2-phenyl-5H-indolo[3,2-d]pyrimidine (800 mg), phosphorous oxychloride (10 mL), and dioxane (10 mL) was refluxed for 40 min. The reaction mixture was concentrated in vacuo and the residue was treated with saturated ammonium chloride and methylene chloride. After drying over magnesium sulfate the solvent was removed in vacuo and the residue was triturated with ether/hexane to afford 4-Chloro-2-phenyl-5H-indolo[3,2-d]pyrimidine (Compound 3) as a white solid.

Workup

  1. temperaturewas refluxed for 40 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue was treated with saturated ammonium chloride and methylene chloride
  4. dry with materialAfter drying over magnesium sulfate the solvent
  5. customwas removed in vacuo
  6. customthe residue was triturated with ether/hexane

Sources & evidence

ORD record
ord-429a5f360ece4ba0848f77f5a31095bc
Source dataset
uspto-grants-1995_10
Patent number
US05463054

Reaction notes

Loading…