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

HRID 1876051Notes

Reaction equation

HRID 1876051 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 190236504-Chloro-6-(1H-1,2,4-triazol-1-yl)pyrimidineYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6f95e84cce954314aa97a9b537d6a185
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

Loading…