Water → 4-Chloro-6-(1H-pyrazol-1-yl)pyrimidine

HRID 1876048Notes

Reaction equation

HRID 1876048 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH:9]1[CH:13]=[CH:12][CH:11]=[N:10]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:8][C:6]1[CH:7]=[C:2]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 10796Cesium carbonateHCID 709434,6-Dichloropyrimidine

Product 1

HCID 106312394-Chloro-6-(1H-pyrazol-1-yl)pyrimidineYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,6-dichloropyrimidine (5.96 g, 40 mmol), 1H-pyrazole (2.72 g, 40.0 mmol), and cesium carbonate (13.03 g, 40.0 mmol) was stirred in DMF (25 mL) at room temperature for 18 h. The reaction was diluted into 100 mL water and extracted with EtOAc. The combined organic layers were concentrated and purified by flash chromatography on a 240 g silica gel cartridge with 0 to 20% ethyl acetate in hexane to yield 4-chloro-6-(1H-pyrazol-1-yl)pyrimidine (4.80 g, 66% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.77 (1H, d, J=0.76 Hz), 8.55 (1H, d, J=2.77 Hz), 7.96 (1H, d, J=1.01 Hz), 7.80 (1H, d, J=1.01 Hz), 6.51 (1H, dd, J=2.64, 1.64 Hz).

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe combined organic layers were concentrated
  3. custompurified by flash chromatography on a 240 g silica gel cartridge with 0 to 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-74e52fecc54441f18ba4bfdef9196ae0
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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