Dimethylformamide → HCID 86686215, compound

HRID 1021246Notes

Reaction equation

HRID 1021246 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)=[CH:4][CH:3]=1.[CH3:13]N(C=O)C.[H-].[Na+].CI>C(Cl)(Cl)Cl.CCOC(C)=O.O>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:9][CH:10]([O:12][CH3:13])[CH2:11]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59139776HCID 59139776, compound

Product 1

HCID 86686215HCID 86686215, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1-(6-Chloropyridazine-3-yl)azetidin-3-ol (599 mg) was mixed with DMF (6 ml), and sodium hydride (55% suspended in oil) (211 mg) was added thereto at 0° C., followed by stirring at 0° C. for 10 minutes. Then, methyl iodide (916 mg) was added thereto at 0° C., followed by stirring at room temperature overnight. To the reaction mixture were added water, EtOAc, and CHCl3, and the organic layer was washed with water and saturated brine, then dried over anhydrous Na2CO3, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain 3-chloro-6-(3-methoxyazetidin-1-yl)pyridazine (323 mg).

Workup

  1. additionwas added
  2. customat 0° C.
  3. customat 0° C.
  4. stirringby stirring at room temperature overnight
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous Na2CO3
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-1f28f23808144029a8fbcf3595700ea7
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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