Methyl iodide → tert-Butyl (1-methyl-6-oxo-1,6-dihydropyridin-3-yl)carbamate

HRID 1925333Notes

Reaction equation

HRID 1925333 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1.[CH3:17]I>CO>[CH3:17][N:8]1[C:3](=[O:2])[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 2763103tert-Butyl (6-methoxypyridin-3-yl)carbamate

Product 1

HCID 15185799tert-Butyl (1-methyl-6-oxo-1,6-dihydropyridin-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl 6-methoxypyridin-3-ylcarbamate (14.4 g, 64.2 mmol) in MeOH (95 mL) was added methyl iodide (14.6 g, 103 mmol). The reaction mixture was heated at reflux for 16 h, cooled to RT and concentrated down. The residue was purified by silica gel chromatography to give the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated down
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1e4faca995fe4d43ad2f8ec58cccdf6a
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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