1,2-Dimethoxyethane → HCID 24901930, Verbindung

HRID 227740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227740
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[C:15](B(O)O)=[CH:14][CH:13]=[CH:12][N:11]=1.COCCOC.C([O-])(O)=O.[Na+]>CCOC(C)=O.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:1][C:2]1[N:7]=[C:6]([C:15]2[C:10]([Cl:9])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 775312,4-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 2762704(2-Chloropyridin-3-yl)boronic acid

Produkt 1

HCID 24901930HCID 24901930, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To 2,4-dichloropyrimidine (2.00 g, 13.4 mmol), 2-choropyridine-3-boronic acid (3.16 g, 20.1 mmol) and Pd(PPh3)4 (1.55 g, 1.30 mmol), was added DME (30.0 ML) and 1 M NaHCO3 (13.0 mL). The resulting mixture was heated to 90° C. for 17 hours, then diluted with EtOAc and extracted with saturated sodium carbonate, water, and brine. The organics were dried over sodium sulfate, filtered and concentrated. The resulting solid was triturated with ether and dried to yield the desired product. MS m/z=226 [M+H]+. Calc'd for C9H5Cl2N4: 225.12.

Aufarbeitung

  1. extractionextracted with saturated sodium carbonate, water, and brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2870f29fe7db4907bbc582cc4a93f57c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560551B2

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