Methyl iodide → HCID 3529665, compound

HRID 377108Notes

Reaction equation

HRID 377108 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 3× 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 5× 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 5× 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-137c883929d34622a6f420d8ea7f37d5
Source dataset
uspto-grants-2000_02
Patent number
US06022884

Reaction notes

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