Diisopropylethylamine → 2-Phenylpyrimidine-4-carboxylic acid

HRID 324973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 324973
Br[C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C>C(O)C.[Pd]>[C:8]1([C:5]2[N:4]=[C:3]([C:14]([OH:16])=[O:15])[CH:2]=[CH:7][N:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 2

HCID 81531DiisopropylethylamineHCID 185215975-Bromo-2-phenylpyrimidine-4-carboxylic acid

Produkt 1

HCID 217091412-Phenylpyrimidine-4-carboxylic acidAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 500 mg 5-bromo-2-phenyl-4-pyrimidinecarboxylic acid and 1 mL N,N-diisopropylethylamine in 5 mL of ethanol was hydrogenated at 40 psi of H2 for 16 hr using 200 mg of 10% palladium-on-carbon as catalyst. The catalyst was filtered off and the ethanol removed by evaporation under reduced pressure. The residue was dissolved in water, acidified with 3 N hydrochloric acid and the precipitate was collected by filtration. This material was air dried to yield 300 mg of 2-phenyl-4-pyrimidinecarboxylic acid as a white solid which was used in the next step without further purification or characterization. A solution of 150 mg of 2-phenyl-4-pyrimidinecarboxylic acid in 1 mL of thionyl chloride was heated at 70° C. for 1 hr, cooled to room temperature and the excess thionyl chloride removed by evaporation under reduced pressure to yield 145 mg of 2-phenyl-4-pyrimidinecarboxylic acid chloride which was used in the next step without further purification or characterization.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customthe ethanol removed by evaporation under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. filtrationthe precipitate was collected by filtration
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e1415bced4a5472bb2f914269642e2ef
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06221871B1

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