Pyrazole → 5-(1H-pyrazol-1-yl)pyrimidin-2-amine

HRID 500155Notes

Reaction equation

HRID 500155 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Br[C:7]1[CH:8]=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1.CNC1CCCCC1NC.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[N:1]1([C:7]2[CH:8]=[N:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamine

Product 1

HCID 672249655-(1H-pyrazol-1-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 1H-pyrazole (0.42 g, 0.0061 mol), 5-bromopyrimidin-2-amine (1.3 g, 7.3 mmol), copper(I) iodide (58.2 mg, 0.306 mmol), N,N′-dimethylcyclohexane-1,2-diamine (0.193 mL, 1.22 mmol), potassium carbonate (1.77 g, 12.8 mmol) in N,N-dimethylformamide (5.00 mL) was irradiated under microwave at 180° C. for 1 h. After cooling, the mixture was purified by chromatography on silica gel with methanol in methylene chloride (0-10%) to afford the desired product. LCMS: (M+H)=162.1.

Workup

  1. customwas irradiated under microwave at 180° C. for 1 h
  2. temperatureAfter cooling
  3. customthe mixture was purified by chromatography on silica gel with methanol in methylene chloride (0-10%)

Sources & evidence

ORD record
ord-a5e62dcd242f49f280f9ec75c6c2e57a
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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