Tetrahydrofuran → HCID 59191511, compound

HRID 447085Notes

Reaction equation

HRID 447085 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[C:6]([CH3:9])[C:7]=1[CH3:8].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17]C#N.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1C[O:33]CC1>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)=[O:33])=[C:6]([CH3:9])[C:7]=1[CH3:8]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 75959Pyridine-2-acetonitrileHCID 2724254Sodium bis(trimethylsilyl)amideHCID 211875053,6-Dichloro-4,5-dimethylpyridazine

Product 1

HCID 59191511HCID 59191511, compoundYield 44%

Procedure

3,6-Dichloro-4,5-dimethyl-pyridazine (1.00 g, 5.65 mmol) is added to a dry 250-ml round-bottom flask under N2 followed by THF (50 mL) and pyridin-2-yl-acetonitrile (800 mg, 7.68 mmol). The reaction is degassed for 30 min. NaHMDS (1.0 M, 14.13 mL, 14.13 mmol) is added and the reaction is stirred overnight. The reaction mixture is transferred to a beaker and air stirred vigorously for several hours. The reaction mixture is quenched with saturated sodium bicarbonate solution. The organics are extracted with dichloromethane. The combined organic layers are washed with brine and dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material is purified via flash chromatography on silica gel (0-20% methanol in CH2Cl2) to afford the title compound (616 mg, 44%).

Workup

  1. customThe reaction is degassed for 30 min
  2. stirringstirred vigorously for several hours
  3. customThe reaction mixture is quenched with saturated sodium bicarbonate solution
  4. extractionThe organics are extracted with dichloromethane
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material is purified via flash chromatography on silica gel (0-20% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-d83443d2c14e44e3be55b480b92cee33
Source dataset
uspto-grants-2013_07
Patent number
US08481542B2

Reaction notes

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