Toluene → 2,4-Dichloro-6-phenylpyrimidine

HRID 75434

Reaktionsgleichung

Reaktionsgleichung von HRID 75434
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>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.CCO>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 773782,4,6-Trichloropyrimidine

Produkt 1

HCID 2415542,4-Dichloro-6-phenylpyrimidineAusbeute 110,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2,4,6-trichloropyrimidine 8 (1 g, 5.45 mmol), phenylboronic acid (665 mg, 5.45 mmol), Pd(PPh3)4 (100 mg) and 2N aqueous Na2CO3 (4.1 mL) in 1:1 toluene:EtOH (15 mL) was heated in a microwave at 120° C. for 20 min. The reaction mixture was diluted with EtOAc and washed with H2O and brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give 2,4-dichloro-6-phenylpyrimidine as a solid (1.35 g), which was used without further purification in the next step.

Aufarbeitung

  1. washwashed with H2O and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6e48fb1f51dd4bb1998a08adfb7be856
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835429B2

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