Methyl iodide → HCID 67272383, compound

HRID 1592477Notes

Reaction equation

HRID 1592477 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[CH:12][NH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:18]I>C1COCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([CH3:18])[CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178453336HCID 178453336, compound

Product 1

HCID 67272383HCID 67272383, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of [2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (512 mg, 2.42 mmol) in THF (20 mL) at −10° C. was added NaH (60%, 97 mg, 2.42 mmol). After stirring at −10° C. for 30 min, MeI (0.14 mL, 2.17 mmol) was added. After stirring at −10° C. for 2.5 h, the reaction mixture was concentrated to afford a yellow oil. Purification by flash column chromatography on silica gel using 2% MeOH/CH2Cl2 afforded [2-(1-methyl-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester as a yellow oil (144 mg, 34%). Deprotection with TFA using General Procedure F gave [2-(lmethyl-1H-imidazol-4-yl)-ethyl]-amine as a yellow oil (51 mg, 25%).

Workup

  1. stirringAfter stirring at −10° C. for 2.5 h
  2. concentrationthe reaction mixture was concentrated
  3. customto afford a yellow oil
  4. customPurification by flash column chromatography on silica gel using 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-5399006b03eb464aacf97d67b2b709d3
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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