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

HRID 219751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219751
[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[CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:24][N:25]1[CH:29]=[N:28][N:27]=[C:26]1[SH:30].[OH-:31].[Li+].[I-].[Na+].CN(C)C=[O:38]>>[C:23]([OH:38])(=[O:31])[CH3:21].[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:30][C:26]3[N:25]([CH3:24])[CH:29]=[N:28][N:27]=3)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 5

HCID 3939Lithium HydroxideHCID 5238Sodium IodideHCID 6228DimethylformamideHCID 690261252-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclopropyl-pyrimidineHCID 178481306HCID 178481306, Verbindung

Produkt 1

HCID 690760382-tert-Butyl-4-{4-[3-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-cyclopropyl-pyrimidine acetate

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

0.7 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclopropyl-pyrimidine (1.45 mmol) and 0.55 g of 4-methyl-4H-[1,2,4]triazole-3-thiol (2.08 mmol) were dissolved in 10 ml of dimethylformamide. After addition of 0.104 g of lithium hydroxide (4.36 mmol) and 0.109 g of sodium iodide (0.73 mmol), the reaction mixture was stirred at 70° C. for 3 h. After cooling, the solvent was evaporated and the residue partitioned between dichloromethane and half-saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The residue was purified via preparative HPLC on a C18-Symmetry column (Waters) with water/methanol (0.1% acetic acid). Fractions containing the product were combined and lyophilised to yield 0.075 g of the product.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. customthe residue partitioned between dichloromethane and half-saturated sodium chloride solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified via preparative HPLC on a C18-Symmetry column (Waters) with water/methanol (0.1% acetic acid)
  8. additionFractions containing the product

Quellen und Nachweise

ORD-Eintrag
ord-ab2aa95b5690499ba8b774fa342168e1
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202868B2

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