Pyrazole → 2-(1H-Pyrazol-1-yl)pyrimidine

HRID 1038120Notes

Reaction equation

HRID 1038120 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Br[C:7]1[N:12]=[CH:11][CH:10]=[CH:9][N:8]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(OCC)(=O)C>CC(N(C)C)=O.[Cu]I.O>[N:1]1([C:7]2[N:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

8

Reactant 4

HCID 1048PyrazoleHCID 13181,10-PhenanthrolineHCID 8857Ethyl AcetateHCID 783452-Bromopyrimidine

Product 1

HCID 111707712-(1H-Pyrazol-1-yl)pyrimidineYield 15.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

A reaction mixture containing pyrazole (2 g, 29 mmol), 2-bromopyrimidine (3.8 g, 24 mmol), copper (I) iodide (0.91 g, 4.8 mmol) and 1,10-phenanthroline (1.7 g, 9.6 mmol) in DMA was heated at 140° C. in a sealed tube for 6 hours. After the reaction, ethyl acetate (30 mL) was added, followed by water. The aqueous layer was extract three times (20 mL) and the organic layer was collected, dry over sodium sulfate. After concentration under vacuum, the crude product was purified using column chromatography (10% ethyl acetate in dichloromethane) to give 0.55 g of pure product. 15% yield. MS (ESMS, M+H 146).

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extract three times (20 mL)
  3. customthe organic layer was collected
  4. dry with materialdry over sodium sulfate
  5. concentrationAfter concentration under vacuum
  6. customthe crude product was purified

Sources & evidence

ORD record
ord-def692fd8412499c9e784ff4a9993002
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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