Sodium Carbonate → 5-Bromo-4-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2ylamine

HRID 28568

Reaktionsgleichung

Reaktionsgleichung von HRID 28568
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([Br:9])=[C:4](Cl)[N:3]=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16](B(O)O)[CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[Br:9][C:5]1[C:6]([Cl:8])=[N:7][C:2]([NH2:1])=[N:3][C:4]=1[C:14]1[CH:13]=[C:12]([Cl:11])[CH:17]=[CH:16][C:15]=1[O:21][CH3:22]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 6182885-Bromo-4,6-dichloropyrimidin-2-amineHCID 27357515-Chloro-2-methoxyphenylboronic acid

Produkt 1

HCID 860043285-Bromo-4-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2ylamineAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a mixture of 2-amino-4,6-dichloro-5-bromo-pyrimidine (1.22 g, 5.0 mmol), 5-chloro-2-methoxy-phenyl boronic acid (1.03 g, 5.5 mmol), palladium (II) acetate (0.17 g, 0.75 mmol) and triphenylphosphine (0.393 g, 1.5 mmol) was added a solution of sodium carbonate (3.18 g, 30 mmol) in water (20 ml) followed by glyme (100 ml). The mixture was stirred under an argon atmosphere at room temperature for 72 hours. Filtration and concentration of the filtrate yielded a residue which was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide 5-bromo-4-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2ylamine (0.40 g, 23% yield) as a beige powder.

Aufarbeitung

  1. filtrationFiltration and concentration of the filtrate
  2. customyielded a residue which
  3. customwas purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-c86dbcde57e04b758ca154d53436c453
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

Verknüpfte Notizen

Wird geladen…