3-Chloro-4-[3-(trifluoromethyl)phenoxy]aniline → 5-(3-chloropropyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1787023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1787023
Cl[C:2]1[C:3]2[N:10]([CH2:11][CH2:12][CH2:13][Cl:14])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)[NH2:19]>C(O)(C)C>[Cl:14][CH2:13][CH2:12][CH2:11][N:10]1[C:3]2[C:2]([NH:19][C:18]3[CH:20]=[CH:21][C:22]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=4)=[C:16]([Cl:15])[CH:17]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=[CH:9]1

Komponenten

4

Edukt 2

HCID 196269843-Chloro-4-[3-(trifluoromethyl)phenoxy]anilineHCID 860848304-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine

Produkt 1

HCID 675204045-(3-chloropropyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amineAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine (789 mg), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (1.09 g) and isopropyl alcohol (5 mL) was stirred at 80° C. for 4.5 hrs. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL) was added to the residue, and the mixture was extracted with ethyl acetate (40 mL×3). The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→20:80) to give the title compound (1.46 g).

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (40 mL×3)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→20:80)

Quellen und Nachweise

ORD-Eintrag
ord-0beab6c844f440e7aaf3b2c5915491bc
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507740B2

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