Dimethylformamide → HCID 86686215, compound

HRID 2171645Notes

Reaction equation

HRID 2171645 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-ad1c8baaa578468485a639299822419f
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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