Sodium hydride → HCID 12237610, compound

HRID 2300898Notes

Reaction equation

HRID 2300898 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[H-].[Na+].[Cl:10][C:11]1[N:12]=[N:13][C:14](Cl)=[CH:15][CH:16]=1>C1COCC1.O.CCOC(C)=O>[Cl:10][C:11]1[N:12]=[N:13][C:14]([O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 766463-(Dimethylamino)-1-propanol

Product 1

HCID 12237610HCID 12237610, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-dimethylamino-propanol (95 μL) in 5 mL of THF at 0° C. was added NaH (20 mg). The mixture was stirred for 5 min; then 3,6-dichloropyridazine (100 mg) was added and the mixture was allowed to warm to room temperature and stirred overnight at this temperature. The mixture was diluted with 5 mL of water and 5 mL of EtOAc, the phases were separated, and the aqueous phase was extracted with 2×5 mL of EtOAc. The combined organics were washed with 5 mL of brine, dried over Na2SO4 and concentrated to a colorless oil (128 mg) that was used without further purification. Mass spectrum (ESI) 215.9 (M+).

Workup

  1. stirringstirred overnight at this temperature
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with 2×5 mL of EtOAc
  4. washThe combined organics were washed with 5 mL of brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a colorless oil (128 mg) that
  7. customwas used without further purification

Sources & evidence

ORD record
ord-cbb1245c24fe49a5adb595af7534355a
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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