Potassium Phosphate, Tribasic → 6-(5-Chloro-2-methoxy-phenyl)-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28547

Reaktionsgleichung

Reaktionsgleichung von HRID 28547
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:5]=[C:4]([NH2:16])[CH:3]=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:27][CH3:28])=[C:22](B(O)O)[CH:23]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([O:27][CH3:28])=[C:20]([C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=3)[N:5]=[C:4]([NH2:16])[CH:3]=2)[CH:19]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 860043166-Chloro-N2-(4-chlorophenyl)pyrimidine-2,4-diamine

Produkt 1

HCID 114852166-(5-Chloro-2-methoxy-phenyl)-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamineAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 6-chloro-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine (0.077 g, 0.30 mmol), 5-chloro-2-methoxy-phenyl boronic acid (0.112 g, 0.60 mmol), palladium (II) acetate (0.017 g, 0.075 mmol), 2-(dicyclohexylphosphino)biphenyl (0.105 g, 0.30 mmol) and potassium phosphate (0.254 g, 1.2 mmol) in dry toluene (3.5 ml) was heated at 90-100° C. under an argon atmosphere for 18 hours. After cooling to room temperature, ether (20 ml) was added and the mixture was washed with aqueous sodium hydroxide solution (1.0 M, 10 ml), with saturated aqueous sodium chloride solution (10 ml), and dried over magnesium sulfate. After concentrating under reduced pressure, the residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide the title compound (0.032 g, 30% yield) as a white powder.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washthe mixture was washed with aqueous sodium hydroxide solution (1.0 M, 10 ml), with saturated aqueous sodium chloride solution (10 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentrating under reduced pressure
  5. customthe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-2a8f2e02149a486185b496f807fc8ddf
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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