Ammonium Chloride → 2-Chloro-4-phenylpyrimidine

HRID 17823

Reaktionsgleichung

Reaktionsgleichung von HRID 17823
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[Br-].[C:10]1([Zn+])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 775312,4-DichloropyrimidineHCID 178419759HCID 178419759, Verbindung

Produkt 1

HCID 6053562-Chloro-4-phenylpyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2,4-dichloropyrimidine (149 mg, 1 mmol) in THF (5 mL), tetrakis(triphenylphosphine) palladium (23 mg, 2 mol %) and 0.5M solution of phenylzinc bromide (2.1 mL, 1.05 mmol) in THF were added. The reaction mixture was stirred at 50° C. for overnight. Then it was added saturated ammonium chloride solution and extracted with EtOAc twice. The organic layers were combined, washed with water and dried (MgSO4). Evaporation of solvent gave a yellow residue which was purified by Prep. HPLC to afford a yellowish oil as 2-chloro-4-phenyl-pyrimidine.

Aufarbeitung

  1. extractionextracted with EtOAc twice
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customEvaporation of solvent
  5. customgave a yellow residue which
  6. customwas purified by Prep

Quellen und Nachweise

ORD-Eintrag
ord-5f20db2624bf42dea12531dc70b7dfbc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741281B2

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