Methyl iodide → HCID 57899324, compound

HRID 425754Notes

Reaction equation

HRID 425754 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]([CH3:17])[C:11]2[CH2:15][O:14][C:13](=[O:16])[CH:12]=2)[CH:5]=[N:6][C:7]=1[Cl:8].[C:18]([Li])(C)(C)C.CI>O1CCCC1.CCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]([CH3:17])[C:11]2[CH:15]([CH3:18])[O:14][C:13](=[O:16])[CH:12]=2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 16752771HCID 16752771, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 57899324HCID 57899324, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

150 mg (0.55 mmol) of 4-[[(5,6-dichloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one (10) are dissolved in 5 ml of tetrahydrofuran and cooled to −78° C., and 339 μl (0.58 mmol) of a 1.7 M solution of tert.-butyllithium in pentane are added. After 30 min of stirring at −78° C., 36 μl (0.58 mmol) of methyl iodide are added, and the mixture is stirred at −78° C. for a further 30 min and then warmed to room temperature. Concentration under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (4:1) gives 48 mg (27% of theory) of 4-[[(5,6-dichloropyridin-3-yl)methyl](methyl)amino]-5-methylfuran-2(5H)-one.

Workup

  1. stirringthe mixture is stirred at −78° C. for a further 30 min
  2. temperaturewarmed to room temperature
  3. concentrationConcentration
  4. customunder reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-c431bb1399b64b80a9a0084106fb5d8f
Source dataset
uspto-grants-2012_01
Patent number
US08106212B2

Reaction notes

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