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Water → HCID 58772825, Verbindung

HRID 271454
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 271454
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:6]([Cl:14])[N:5]=[CH:4][N:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:14][C:6]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)[N:3]=[CH:4][N:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 58772827HCID 58772827, Verbindung

Produkt 1

HCID 58772825HCID 58772825, VerbindungAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 4,6-dichloro-5-(pyridin-4-yl)pyrimidine (1.07 g, 4.8 mmol), 4-chlorophenylboronic acid (740 mg, 4.8 mmol) and tetrakis(triphenylphosphine)palladium (550 mg, 0.48 mmol) in toluene (10 mL) at room temperature under argon was added aqueous Na2CO3 solution (2 M, 5 mL, 10 mmol). The resulting mixture was stirred at 100° C. under argon for 15 h. Analysis by HPLC/MS indicated that the reaction was complete. After the reaction mixture was cooled to room temperature, water (25 mL) was added. The resulting mixture was extracted with EtOAc (2×25 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain the title compound (1.12 g, HPLC purity about 92%) as a white solid. 1H NMR (CDCl3): δ7.18 (d, 2H), 7.2-7.3 (m, 4H), 8.66 (d, 2H), 9.07 (s, 1H).

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionThe resulting mixture was extracted with EtOAc (2×25 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9493d09e377a4fd2ab0795e558f38775
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07452892B2

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