1-Bromo-3,5-bis(trifluoromethyl)benzene → 4-(3,5-Bis(trifluoromethyl)phenyl)-6-propylpyrimidine-2-carbonitrile

HRID 733169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733169
[CH2:1]([C:4]1[CH:9]=[C:8]([Sn](C)(C)C)[N:7]=[C:6]([C:14]#[N:15])[N:5]=1)[CH2:2][CH3:3].[F:16][C:17]([F:30])([F:29])[C:18]1[CH:19]=[C:20](Br)[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:16][C:17]([F:30])([F:29])[C:18]1[CH:19]=[C:20]([C:8]2[CH:9]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]=[C:6]([C:14]#[N:15])[N:7]=2)[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1

Komponenten

5

Edukt 2

HCID 676021-Bromo-3,5-bis(trifluoromethyl)benzeneHCID 690493004-Propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile

Produkt 1

HCID 498624214-(3,5-Bis(trifluoromethyl)phenyl)-6-propylpyrimidine-2-carbonitrileAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Bis(triphenylphosphine)palladium dichloride (34 mg, 0.05 mmol) was added under a nitrogen atmosphere to a mixture of 4-propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile (155 mg, 0.50 mmol) and 3,5-bis-trifluoromethyl-bromobenzene (0.10 mL, 0.58 mmol) in dimethylformamide (3 mL). The mixture was refluxed for 4 hours then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent: DCM) to afford a solid which was triturated in pentane. After filtration, 4-(3,5-bis-trifluoromethyl-phenyl)-6-propyl-pyrimidine-2-carbonitrile (63 mg, 35%) was obtained as an off white solid (mp=112° C.).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 4 hours
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. concentrationThe combined organic layers were concentrated under reduced pressure
  6. customThe residue was chromatographed over silica gel (eluent: DCM)
  7. customto afford a solid which
  8. customwas triturated in pentane
  9. filtrationAfter filtration

Quellen und Nachweise

ORD-Eintrag
ord-325d58f3933544e78d8062c1a27aa91d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589095B2

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