Sodium hydride → HCID 13822269, compound

HRID 1904253Notes

Reaction equation

HRID 1904253 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[N:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[C:20]([N:24]1[C:29](=[O:30])[C:28]([CH3:31])=[C:27](Cl)[CH:26]=[N:25]1)([CH3:23])([CH3:22])[CH3:21]>CN(C)C=O>[C:20]([N:24]1[C:29](=[O:30])[C:28]([CH3:31])=[C:27]([O:15][CH2:14][C:11]2[CH:12]=[N:13][C:8]([O:7][CH2:6][C:5]3[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)[CH:26]=[N:25]1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 138222642-tert-butyl-5-chloro-4-methylpyridazin-3-(2H)-oneHCID 13822268HCID 13822268, compound

Product 1

HCID 13822269HCID 13822269, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2.3 g of 6-(4-fluorobenzyloxy)-3-pyridine methanol in 20 ml of N,N-dimethylformamide was added under stirring at 0° C. 0.5 g of 55% sodium hydride (in mineral oil). After stirring for 30 minutes at room temperature, thereto was added dropwise a solution of 2.0 g of 2-t-butyl-5-chloro-4-methyl-3(2H)-pyridazinone in 5 ml of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for additional 8 hours, poured into 50 ml of ice water and extracted twice with 50 ml of benzene. The organic layer was washed with water, dried over anhydrous sodium sulfate and then freed of solvent by distillation under reduced pressure to give 3.8 g of a crude product. The crude product was separated and purified through thin layer chromatography (on silica gel; benzene) to obtain 2.5 g of 2-t-butyl-5-[{6-(4-fluorobenzyloxy)-3-pyridyl}-methyloxy]-4-methyl-3(2H)-pyridazinone as an oil.

Workup

  1. stirringAfter stirring for 30 minutes at room temperature
  2. stirringThe reaction mixture was stirred at room temperature for additional 8 hours
  3. extractionextracted twice with 50 ml of benzene
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationfreed of solvent by distillation under reduced pressure
  7. customto give 3.8 g of a crude product
  8. customThe crude product was separated
  9. custompurified through thin layer chromatography (on silica gel; benzene)

Sources & evidence

ORD record
ord-04b9c686403d4530a1434ae7d1768e95
Source dataset
uspto-grants-1989_06
Patent number
US04837217

Reaction notes

Loading…