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Sodium Carbonate → 4-Chloro-6-(2-methylpyridin-3-yl)pyrimidine

HRID 2174172
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2174172
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14][CH:13]=[CH:12][N:11]=1.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>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.C(#N)C>[Cl:8][C:6]1[CH:7]=[C:2]([C:15]2[C:10]([CH3:9])=[N:11][CH:12]=[CH:13][CH:14]=2)[N:3]=[CH:4][N:5]=1
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Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 709434,6-DichloropyrimidineHCID 517044Potassium AcetateHCID 164142712-Methylpyridine-3-boronic acid, pinacol ester

Produkt 1

HCID 898585944-Chloro-6-(2-methylpyridin-3-yl)pyrimidineAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

First, 3.01 g of 4,6-dichloropyrimidine, 10.9 g of 2-methylpyridine-3-boronic acid pinacol ester, 60 mL of 1M aqueous solution of potassium acetate, 60 mL of 1M aqueous solution of sodium carbonate, and 60 mL of acetonitrile were put in a 300 mL three-neck flask, and the air in the flask was replaced with argon. To this mixture, 1.40 g of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was irradiated with microwaves under conditions of 70° C. and 400 W and for 2 hours to cause a reaction. This reaction mixture was extracted with ethyl acetate, and washing with saturated brine was performed. Anhydrous magnesium sulfate was added to the obtained solution of the extract for drying, and the resulting mixture was gravity-filtered to give a filtrate. A residue obtained by condensing the filtrate was purified by flash column chromatography using ethyl acetate as a developing solvent. A solid obtained by condensing the fraction was purified by flash column chromatography using hexane and ethyl acetate in a ratio of 1:1 as a developing solvent, so that 4-chloro-6-(2-methylpyridin-3-yl)pyrimidine was obtained (a yellow white solid, yield of 24%). A synthetic scheme of Step 1 is shown in (c-1) below.

Aufarbeitung

  1. customthe mixture was irradiated with microwaves under conditions of 70° C. and 400 W and for 2 hours
  2. customa reaction
  3. extractionThis reaction mixture was extracted with ethyl acetate
  4. washwashing with saturated brine
  5. additionAnhydrous magnesium sulfate was added to the obtained solution of the
  6. extractionextract
  7. customfor drying
  8. filtrationthe resulting mixture was gravity-filtered
  9. customto give a filtrate
  10. customA residue obtained by condensing the filtrate
  11. customwas purified by flash column chromatography
  12. customA solid obtained by condensing the fraction
  13. customwas purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bae732c602fe42d4b1b40e1ee13065e3
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09059414B2

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