Imidazole → 2-Amino-5-imidazol-1-ylpyridine-3-carbaldehyde

HRID 241420Notes

Reaction equation

HRID 241420 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5](I)=[CH:4][N:3]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.CN(C)[C@@H]1CCCC[C@H]1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.[Cu](I)I.C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 62657Potassium Phosphate, TribasicHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamineHCID 177501772-Amino-5-iodopyridine-3-carbaldehyde

Product 1

HCID 866648072-Amino-5-imidazol-1-ylpyridine-3-carbaldehyde

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

300 mg (1.210 mmol) of 2-amino-5-iodopyridine-3-carbaldehyde and 24 mg (3.629 mmol) of imidazole are dissolved in ml of DMSO in a nitrogen-filled microwave vessel. 51.6 mg (0.363 mmol) of trans-N,N-dimethyl-1,2-cyclohexanediamine, 69.1 mg (0.363 mmol) of copper iodide, 523.8 mg (2.468 mmol) of K3PO4 and 5 ml of toluene is added. The reaction mixture is irradiated with microwaves for 2 hours at 150° C. The reaction mixture is cooled to room temperature, filtered off, and the solvent is removed. Water/ethyl acetate is added to the residue. The organic phase is separated, and the aqueous phase is extracted a further 2× with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered, and the solvent is removed, giving 2-amino-5-imidazol-1-ylpyridine-3-carbaldehyde; HPLC-MS [M+H]+ 189.2.

Workup

  1. additionfilled microwave vessel
  2. customThe reaction mixture is irradiated with microwaves for 2 hours at 150° C
  3. filtrationfiltered off
  4. customthe solvent is removed
  5. additionWater/ethyl acetate is added to the residue
  6. customThe organic phase is separated
  7. extractionthe aqueous phase is extracted a further 2× with ethyl acetate
  8. dry with materialThe combined organic phases are dried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent is removed

Sources & evidence

ORD record
ord-7e520faa13814f3496d3a9faf54ba095
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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