4-Methylpyrazole → HCID 67225261, compound

HRID 1257801Notes

Reaction equation

HRID 1257801 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Br[C:8]1[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.CNC1CCCCC1NC.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:8]2[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 34064-MethylpyrazoleHCID 11430Potassium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamine

Product 1

HCID 67225261HCID 67225261, compound

Reagents, catalysts & solvents 2

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

Procedure

A suspension of 4-methyl-1H-pyrazole (0.72 g, 0.0088 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 (5.0 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)=176.0.

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-6d2104f0aae34bc1817540ec1071eae9
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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