Methyl iodide → Tert-butyl methyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

HRID 391104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391104
[CH3:1][C:2]1([CH3:23])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:13][CH:14]=2)[O:3]1.CI.[C:26](=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:26][N:15]([C:12]1[N:11]=[CH:10][C:9]([B:4]2[O:3][C:2]([CH3:23])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:14][N:13]=1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]

Komponenten

4

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 177502232-(tert-Butoxycarbonylamino)pyrimidine-5-boronic acid, pinacol ester

Produkt 1

HCID 58234002Tert-butyl methyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

Versuchsvorschrift

Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-ylcarbamate (250 mg) was treated with 3 equivalents methyl iodide and cesium carbonate at room temperature for one hour. The crude reaction mixture was extracted with ethyl acetate and water. The initial organic layer is discarded. The aqueous layer was acidified to pH 5 and the product was extracted out of the aqueous with ethyl acetate. This organic layer was dried with magnesium sulfate, filtered and concentrated to give 150 mg crude tert-butyl methyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-ylcarbamate.

Aufarbeitung

  1. customThe crude reaction mixture
  2. extractionwas extracted with ethyl acetate and water
  3. extractionthe product was extracted out of the aqueous with ethyl acetate
  4. dry with materialThis organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-65a92f57c4ec4e1b98feb4930f78565f
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383620B2

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