Methyl iodide → HCID 10537009, compound

HRID 985481Notes

Reaction equation

HRID 985481 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:18]I>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH3:18])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11367776tert-Butyl (6-methylpyridin-2-yl)carbamate

Product 1

HCID 10537009HCID 10537009, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(tert-Butoxy)-N-(6-methyl(2-pyridyl))carboxamide (20.2 g, 102 mmol) dissolved in N,N-dimethylformamide (75 ml) was slowly added to a suspension of sodium hydride (3.67 g, 153 mmol) in DMF (150 ml) at 0° C. The reaction mixture was warmed to room temperature and stirred for 1 h. Methyl iodide (9.5 ml, 153 mmol) was added dropwise at 0° C. After stirring at room temperature for 16 h, the reaction mixture was poured over ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered, and evaporated under vacuum. The crude product was chromatographed over silica gel to yield 15.3 g (66%) of (tert-Butoxy)-N-methyl-N-(6-methyl(2-pyridyl))carboxamide. NMR 1H Cl3CD δ: 7.50 (t, 1H, J=7.6 Hz), 7.37 (d, 1H, J=7.6 Hz), 6.85 (d, 1H, J=7.6 Hz), 3.38 (s, 3H), 2.48 (s, 3H), 1.50 (s, 9H).

Workup

  1. stirringAfter stirring at room temperature for 16 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-f06469945f1a486185d27c60f3d21659
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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