Lithium Hydroxide → 2-tert-Butyl-4-{4-[3-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-cyclobutylpyrimidine

HRID 219747

Reaktionsgleichung

Reaktionsgleichung von HRID 219747
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19]Cl)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][N:26]1[CH:30]=[N:29][N:28]=[C:27]1[SH:31].[OH-].[Li+].[I-].[K+]>CN(C)C=O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][S:31][C:27]3[N:26]([CH3:25])[CH:30]=[N:29][N:28]=3)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 3939Lithium HydroxideHCID 4875Potassium IodideHCID 666731042-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidineHCID 178481306HCID 178481306, Verbindung

Produkt 1

HCID 115681542-tert-Butyl-4-{4-[3-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-cyclobutylpyrimidineAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.8 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidine (2.28 mmol), 0.29 g of 4-methyl-3-mercapto-1,2,4-triazole (2.52 mmol), 0.15 g of lithium hydroxide and a tip of a spatula of potassium iodide were dissolved in 20 ml of dimethylformamide. The mixture was stirred for 14 h at room temperature and then extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness. The residue was then purified by column chromatography on silica gel (dichloromethane-methanol (2-10%)) to yield an oily residue that was precipitated with acetonitrile thereby yielding 0.46 g of the title compound (47%).

Aufarbeitung

  1. extractionextracted with water and ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was then purified by column chromatography on silica gel (dichloromethane-methanol (2-10%))
  6. customto yield an oily residue that
  7. customwas precipitated with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-02dd9ebd37574f9fb31f0a290af4abce
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202868B2

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