Pyridine → 2-Cyano-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester

HRID 900238Notes

Reaction equation

HRID 900238 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8](I)=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2].[N:13]1C=CC=C[CH:14]=1>>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([C:14]#[N:13])=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 1049PyridineHCID 178470396HCID 178470396, compound

Product 1

HCID 1784703942-Cyano-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester

Conditions

Temperature
110 °C

Procedure

To a solution of 1 g 2-Iodo-5-methyl-3H-imidazole-4-carboxylic acid ethyl ester in 3 ml pyridine 640 mg CuCN were added and the mixture stirred for 3 h at 110° C. Then the pyridine was removed under reduced pressure and the residue was directly purified by chromatography on silica eluting with DCM/MeOH 97:3. Yield: 494 mg.

Workup

  1. customThen the pyridine was removed under reduced pressure
  2. customthe residue was directly purified by chromatography on silica eluting with DCM/MeOH 97:3

Sources & evidence

ORD record
ord-9a2880d9c85343aa94cb5cd7092eb253
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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