Sodium Carbonate → 4-(3-Chloro-phenyl)-2-methoxymethyl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine

HRID 230939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230939
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][N:15]=3)[CH2:10][CH2:9]2)[N:5]=[C:4]([CH2:24][O:25][CH3:26])[N:3]=1.[Cl:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[Cl:27][C:28]1[CH:33]=[C:32]([C:2]2[CH:7]=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([C:14]4[C:19]([C:20]([F:22])([F:21])[F:23])=[CH:18][CH:17]=[CH:16][N:15]=4)[CH2:10][CH2:9]3)[N:5]=[C:4]([CH2:24][O:25][CH3:26])[N:3]=2)[CH:31]=[CH:30][CH:29]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 577610444-Chloro-2-methoxymethyl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine

Produkt 1

HCID 577611754-(3-Chloro-phenyl)-2-methoxymethyl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Combine 4-chloro-2-methoxymethyl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine (388 mg, 1 mmol), 3-chlorophenylboronic acid (157 mg, 1 mmol), Pd(P(Ph)3)4 (100 mg, 0.09 mmol), 2M aqueous sodium carbonate (1 mL), and 1,2-dimethoxyethane (5 mL) under nitrogen. Reflux for 16 hours. Evaporate and add water (5 mL), and extract with EtOAc. Dry the organic layer with sodium sulfate and purify by liquid chromatography, to obtain 4-(3-chloro-phenyl)-2-methoxymethyl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine as a white solid.

Aufarbeitung

  1. temperatureReflux for 16 hours
  2. customEvaporate
  3. additionadd water (5 mL)
  4. extractionextract with EtOAc
  5. dry with materialDry the organic layer with sodium sulfate
  6. custompurify by liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e24e54ad70834497b090fc26470402cf
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566712B2

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