2-Methylaziridine → HCID 85999420, compound

HRID 1392907Notes

Reaction equation

HRID 1392907 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[CH3:10][CH:11]1[CH2:13][NH:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:12]2[CH2:13][CH:11]2[CH3:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 63772-MethylaziridineHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 85999420HCID 85999420, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (352 mg, 2.17 mmole) in 4 mL of dry acetonitrile is 0.4 mL (4.34 mmol) of 2-methyl-aziridine followed by 300 mg (2.17 mmol) of potassium carbonate. The reaction is heated at 60° C. for 20 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 66 mg (17% yield) of 2-Chloro-5-(2-methyl-aziridin-1-ylmethyl)-pyridine. Diagnostic 1H NMR (400 MHz, CDCl3) 1.15 (d, 3H, J=5.4 Hz), 1.34 (d, 1H, J=6.6 Hz), 1.47–1.55 (m, 2H), 3.35 (abq, 2H, J=5.8 Hz), 7.25 (d, 1H, J=6.3 Hz), 7.65 (dd, 1H, J=8.3 and 2.5 hz), 8.27 (d, 1H, J=1.7 Hz); MS 183.2 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is quenched with 5 mL of water
  3. extractionextracted three-times with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customConcentration of the solvent provided an oil which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-3bd68c8f3491460e8aaad2f60666d210
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

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