Tripropylamine → HCID 178441234, Verbindung

HRID 253705

Reaktionsgleichung

Reaktionsgleichung von HRID 253705
[C:1]([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[NH:8][C:7](=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:24])=O.C(N(CCC)CCC)CC>>[C:1]([C:5]1([Cl:24])[NH:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])=[N:8][CH:7]=[CH:6]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 7616TripropylamineHCID 24813Phosphorus oxychlorideHCID 1361571906-tert-Butyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-one

Produkt 1

HCID 178441234HCID 178441234, VerbindungAusbeute 66 %

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A solution of 6-tert-butyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-one (0.47 g, 1.59 mmol) in phosphorous oxychloride (1.65 mL, 15.9 mmol) was treated with tri-n-propylamine (0.61 mL, 3.17 mmol) and heated at 110-120° C. for 1 hour. The solvent was removed by evaporation then azeotroped three times with toluene. 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 (0.33 g, 66% yield) as a yellow oil.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-135cbbe0ce6c44c7ae3e2d00695678d9
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872129B2

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