Tripropylamine → 4-Chloro-6-methyl-2-(2-trifluoromethyl-phenyl)-pyrimidine

HRID 253702

Reaktionsgleichung

Reaktionsgleichung von HRID 253702
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[NH:5][C:4](=O)[CH:3]=1.P(Cl)(Cl)([Cl:21])=O.C(N(CCC)CCC)CC>>[Cl:21][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[N:5]=1

Komponenten

4

Edukt 3

HCID 7616TripropylamineHCID 24813Phosphorus oxychlorideHCID 1358508354(3H)-Pyrimidinone, 6-methyl-2-[2-(trifluoromethyl)phenyl]-

Produkt 1

HCID 219392714-Chloro-6-methyl-2-(2-trifluoromethyl-phenyl)-pyrimidineAusbeute 84,1 %

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A solution of 6-methyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-one (10.7 g, 41.9 mmol) in phosphorous oxychloride (39 mL, 419 mmol) was treated with tri-n-propylamine (16 mL, 83.9 mmol) and refluxed at 110-120° C. for 1 hours. The solvent was evaporated, azeotroped three times with toluene, then dried in vacuo. The residue was taken up in ethyl acetate, washed sequentially with 1 N sodium hydroxide, water and brine, then dried over sodium sulfate and concentrated. Purification by flash chromatography [SiO2, ethyl acetate:hexanes (1:9)] provided the title compound (9.61 g, 84% yield) as an orange oil.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customazeotroped three times with toluene
  3. customdried in vacuo
  4. washwashed sequentially with 1 N sodium hydroxide, water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by flash chromatography [SiO2, ethyl acetate:hexanes (1:9)]

Quellen und Nachweise

ORD-Eintrag
ord-9bdff50eafca4cbbb0601d2dc0730ab9
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872129B2

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