Phosphorus oxychloride → HCID 12690396, compound

HRID 241080Notes

Reaction equation

HRID 241080 reaction equation
[C:1]1([NH:7][C:8]2[N:13]=[CH:12][N:11]=[C:10](O)[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:10]1[N:11]=[CH:12][N:13]=[C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516393HCID 178516393, compound

Product 1

HCID 12690396HCID 12690396, compound

Conditions

Temperature
95 °C

Procedure

6-(Phenylamino)pyrimidin-4-ol (253 mg, 1.35 mmol) was dissolved in neat phosphorous oxychloride (5 mL) and stirred for 3 h at 95° C. then cooled to room temperature and concentrated. The residue was poured into an ice water slurry and extracted with dichloromethane. The extract was washed saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and the solvent evaporated to afford 6-chloro-N-phenylpyrimidine-4-amine (220 mg) which was used without further purification.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated
  3. additionThe residue was poured into an ice water slurry
  4. extractionextracted with dichloromethane
  5. washThe extract was washed saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-e1dd360d0645450aaf15e5943cdc3a49
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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