Methyl iodide → HCID 3529665, compound

HRID 2271294Notes

Reaction equation

HRID 2271294 reaction equation
[H-].[Na+].[CH:3]1([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:19]I>CN(C)C=O>[CH:3]1([N:9]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=2)[CH3:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2615382-Cyclohexylamino-5-nitropyridine

Product 1

HCID 3529665HCID 3529665, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.38 g, 9.48 mmol) was washed 3x with hexanes then a solution of 2-cyclohexylamino-5-nitropyridine (1.88 g, 8.5 mmol) dissolved in dimethylformamide (20 mL) was added. After stirring for 30 minutes at 22° C., the reaction mixture was cooled to 0° C. and methyl iodide (0.55 mL, 8.9 mmol) was added. The solution was stirred for 1.5 hours at 0° C. followed by quenching with saturated aqueous NH4Cl. The reaction mixture was diluted with ethyl acetate and extracted 5x with water (200 mL), saturated NaCl, dried over Na2SO4 and concentrated in vacuo oil was chromatographed on SiO2 using 2:1 hexanes/ethyl acetate as eluent.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. stirringThe solution was stirred for 1.5 hours at 0° C.
  4. customby quenching with saturated aqueous NH4Cl
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. extractionextracted 5x with water (200 mL), saturated NaCl
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo oil
  9. customwas chromatographed on SiO2 using 2:1 hexanes/ethyl acetate as eluent

Sources & evidence

ORD record
ord-b58dd17c15ce45208a4e5a58fabc6125
Source dataset
uspto-grants-2001_12
Patent number
US06333341B1

Reaction notes

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