Potassium Carbonate → 7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

HRID 1853039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1853039
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[N:34][NH:35][CH:36]=2)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:23][N:20]1[CH2:21][CH2:22][CH:17]([C:14]2[CH:15]=[CH:16][C:11]([C:4]3[N:3]=[C:2]([C:32]4[CH:33]=[N:34][NH:35][CH:36]=4)[N:7]4[CH:8]=[CH:9][N:10]=[C:6]4[CH:5]=3)=[CH:12][CH:13]=2)[CH2:18][CH2:19]1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 866853235-Chloro-7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidine

Produkt 1

HCID 674561367-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidineAusbeute 23,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5-Chloro-7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidine (0.120 g, 0.367 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.107 g, 0.551 mmol) and potassium carbonate (0.152 g, 1.10 mmol) were suspended in a mixture of DME (5 mL) and water (2 mL) and purged with argon for 5 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.02121 g, 0.01836 mmol) was added and the reaction sealed and heated at 100° C. for 18 hours. The reaction mixture was cooled to ambient temperature and diluted with water and filtered. The solids were washed with acetone and then dried under high vacuum to afford 7-(4-(1-methylpiperidin-4-yl)phenyl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (0.0310 g, 0.0865 mmol, 23.55% yield). MS (apci) m/z=359.2 (M+H).

Aufarbeitung

  1. custompurged with argon for 5 minutes
  2. customthe reaction sealed
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. filtrationfiltered
  5. washThe solids were washed with acetone
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-391afdf624ad4596999252c9ebb304f2
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962596B2

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