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Potassium Carbonate → methyl 4-(2,5-dimethylpyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylate

HRID 60136
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 60136
CC1(C)C(C)(C)OBO1.Br[C:11]1[CH:12]=[N:13][N:14]([CH3:20])[C:15]=1[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+].Cl[C:28]1[C:33]([CH3:34])=[CH:32][N:31]=[C:30]([CH3:35])[N:29]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O.O1CCOCC1.C(N(CC)CC)C>[CH3:35][C:30]1[N:31]=[C:32]([C:11]2[CH:12]=[N:13][N:14]([CH3:20])[C:15]=2[C:16]([O:18][CH3:19])=[O:17])[C:33]([CH3:34])=[CH:28][N:29]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 11430Potassium CarbonateHCID 673643Methyl 4-bromo-1-methyl-1H-pyrazole-5-carboxylateHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolane2×HCID 124653814-Chloro-2,5-dimethylpyrimidine

Produkt 1

HCID 90383435methyl 4-(2,5-dimethylpyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylateAusbeute 110 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysatorHCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (1.5 ml) was added to a 1,4-dioxane (19 ml) solution of methyl 4-bromo-1-methyl-1H-pyrazole-5-carboxylate (1.9 g), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.15 g), Tris(dibenzylideneacetone)dipalladium(0) (0.16 g), and triethylamine (3.7 ml). The obtained mixture was stirred in a nitrogen atmosphere at 100° C. for 30 minutes. Thereafter, 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.5 ml) was added to the reaction solution, and the obtained mixture was then stirred for 30 minutes at the same temperature as described above. Thereafter, an aqueous solution (3.9 ml) of potassium carbonate (3.6 g) and a 1,4-dioxane (4 ml) solution of 4-chloro-2,5-dimethylpyrimidine (1.0 g) were successively added to the reaction solution, and the obtained mixture was then stirred at the same temperature as described above for 1 hour. Thereafter, water was added to the reaction solution, and the mixed solution was extracted with ethyl acetate and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=3:1-1:1-0:1), so as to obtain the title compound (1.9 g) in the form of an orange liquid.

Aufarbeitung

  1. stirringthe obtained mixture was then stirred for 30 minutes at the same temperature
  2. stirringthe obtained mixture was then stirred at the same temperature
  3. customas described above for 1 hour
  4. extractionthe mixed solution was extracted with ethyl acetate
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=3:1-1:1-0:1)

Quellen und Nachweise

ORD-Eintrag
ord-703c64c185294d3fb38394e58541bf0b
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440970B2

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