Sodium Carbonate → 6-(5-Chloro-2-methoxy-phenyl)-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28529

Reaktionsgleichung

Reaktionsgleichung von HRID 28529
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[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(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>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([O:27][CH3:28])=[C:20]([C:2]2[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[CH:3]=2)[CH:19]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 14842856-chloro-4-N-(4-chlorophenyl)pyrimidine-2,4-diamineHCID 27357515-Chloro-2-methoxyphenylboronic acid

Produkt 1

HCID 114398336-(5-Chloro-2-methoxy-phenyl)-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamineAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
92.5 °C

Versuchsvorschrift

To a mixture of 6-chloro-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine (0.5 g, 1.96 mmol), 5-chloro-2-methoxy-phenyl boronic acid (0.73 g, 3.92 mmol), palladium (II) acetate (0.066 g, 0.294 mmol), and triphenylphosphine (0.154 g, 0.588 mmol) was added a solution of sodium carbonate (0.63 g, 5.88 mmol) dissolved in water (6 ml) followed by glyme (20 ml). The reaction mixture was stirred under an argon atmosphere at 90-95° C. for 18 hours. After cooling to room temperature, the mixture was filtered through a pad of celite under suction and concentrated. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide the title compound (0.350 g, 49% yield) as a white powder. 1H NMR (CDCl3) δ 3.86 (s, 3H, CH3), 4.90 (s, 2H, NH2), 6.58 (s, 1H, NH), 6.71 (s, 1H, Ar), 6.91 (d, 1H, J=8.8 Hz, Ar), 7.32-7.41 (m, 5H, Ar), 7.87 (d, 1H, J=2.7 Hz, Ar).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through a pad of celite under suction
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-3cff5c96b7894489880218862199ea5a
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

Verknüpfte Notizen

Wird geladen…