1H-1,2,4-Triazole → 4-Chloro-6-(1H-1,2,4-triazol-1-yl)pyrimidine

HRID 1876051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876051
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH:9]1[CH:13]=[N:12][CH:11]=[N:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:8][C:6]1[CH:7]=[C:2]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)[N:3]=[CH:4][N:5]=1

Komponenten

6

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 709434,6-Dichloropyrimidine

Produkt 1

HCID 190236504-Chloro-6-(1H-1,2,4-triazol-1-yl)pyrimidineAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4,6-dichloropyrimidine (5.96 g, 40 mmol), 1H-1,2,4-triazole (1.381 g, 20.00 mmol), and cesium carbonate (13.03 g, 40.0 mmol) was stirred in DMF (25 mL) at room temperature for 16 h. The reaction was diluted with 100 mL water and extracted with EtOAc. The combined organic extracts were concentrated and purified by flash chromatography on a 160 g silica gel cartridge with 25 to 50% EtOAc in hexane to yield 4-chloro-6-(1H-1,2,4-triazol-1-yl)pyrimidine (2.78 g, 38% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.21 (1H, s), 8.87 (1H, s), 8.15 (1H, s), 7.91 (1H, s). LCMS: RT=0.68 min, MH+=182.1.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. concentrationThe combined organic extracts were concentrated
  3. custompurified by flash chromatography on a 160 g silica gel cartridge with 25 to 50% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-6f95e84cce954314aa97a9b537d6a185
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309577B2

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