Phosphorus oxychloride → 2-Chloro-4,5-diphenylpyrimidine

HRID 12571

Reaktionsgleichung

Reaktionsgleichung von HRID 12571
C[N:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[N:4][C:3]1=O.P(Cl)(Cl)([Cl:23])=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:23][C:3]1[N:2]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][N:4]=1

Komponenten

4

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 36093525,6-Diphenyl-1-methyl-2(1H)-pyrimidinone

Produkt 1

HCID 126742762-Chloro-4,5-diphenylpyrimidine

Versuchsvorschrift

A solution of 1-methyl-5,6-diphenyl-1H-pyrimidin-2-one (106, 314 mg, 1.20 mmol), phosphorus oxychloride (0.6 ml, 6.4 mmol) and phosphorus pentachloride (55 mg, 0.26 mmol) was heated at 120° C. for 3 hours. The excess amount of phosphorus oxychloride was removed under reduced pressure and cold water was added to the residue. The resulting precipitate was extracted with CH2Cl2. The organic layer was washed with brine, and dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (20% ethyl acetate in hexane) to produce the title compound as a white solid.

Aufarbeitung

  1. customThe excess amount of phosphorus oxychloride was removed under reduced pressure and cold water
  2. additionwas added to the residue
  3. extractionThe resulting precipitate was extracted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c92f9d8542fc4ac49029ecc678997a58
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728014B2

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