Acetic Acid → N-[3-bromo-5-(difluoromethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine

HRID 1040032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040032
C(O)(=O)C.[Br:5][C:6]1[CH:7]=[C:8]([CH:10]=[C:11]([CH:13]([F:15])[F:14])[CH:12]=1)[NH2:9].Cl[C:17]1[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=1>O1CCOCC1.C(OCC)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]([NH:9][C:17]2[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=2)[CH:10]=[C:11]([CH:13]([F:14])[F:15])[CH:12]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 584563863-Bromo-5-(difluoromethyl)aniline

Produkt 1

HCID 86658250N-[3-bromo-5-(difluoromethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amineAusbeute 34,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

Acetic acid (1.01 mL, 17.6 mmol) was added to a mixture of 3-bromo-5-(difluoromethyl)aniline (1.30 g, 5.86 mmol) and 2-chloro-4-(trifluoromethyl)pyrimidine (2.14 g, 11.7 mmol) in dioxane (5.0 mL). The mixture was heated to 105° C. for 16 hrs then cooled to room temperature. The mixture was diluted with ethyl acetate, washed with dilute aqueous NaHCO3, brine and dried. The residue was purified by chromatography on silica gel (0-15% ethyl acetate in hexanes) to yield N-[3-bromo-5-(difluoromethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (741 mg, 2.01 mmol, 34%).

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. washwashed with dilute aqueous NaHCO3, brine
  3. customdried
  4. customThe residue was purified by chromatography on silica gel (0-15% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c40b77ecf381443c9872e509a446d0f4
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551984B2

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