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

HRID 1725588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1725588
[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. 1H NMR (CDCl3, 500 MHz) δ 2.63 (3H, s), 7.26 (s, 1H), 7.61 (t, J=7.6 Hz, 1H), 7.67 (t, J=7.5 Hz, 1H), 7.76 (d, J=7.6 Hz, 1H), 7.82 (d, J=7.8 Hz, 1H) ppm; MS (FIA) 273.0 (M+H); Rt (Method A) 3.499 min.

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-d7ab3e427cb94432b8a06fa89559366e
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491730B2

Notizen zur Reaktion

Wird geladen…