Tetrahydrofuran → HCID 59191601, compound

HRID 1479959Notes

Reaction equation

HRID 1479959 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]=[C:13]([CH2:17]C#N)[CH:12]=1.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:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)=[O:33])=[C:6]([CH3:9])[C:7]=1[CH3:8]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 809233-PyridineacetonitrileHCID 2724254Sodium bis(trimethylsilyl)amideHCID 211875053,6-Dichloro-4,5-dimethylpyridazine

Product 1

HCID 59191601HCID 59191601, compoundYield 93%

Procedure

3,6-Dichloro-4,5-dimethyl-pyridazine (1.00 g, 5.65 mmol) is added to an oven-dried, 250-mL round-bottom flask under N2 followed by THF (50 mL) and pyridin-3-yl-acetonitrile (800 mg, 7.68 mmol). The reaction is degassed with a flow of N2 for 30 min. NaHMDS (14.13 mL, 1.0 M, 14.13 mmol) is added and the reaction is stirred for 16 h. The reaction mixture is then transferred to a beaker and stirred vigorously under open to the atmosphere for several hours. The reaction is quenched with saturated sodium bicarbonate solution, and the organics are extracted with dichloromethane. The combined organic layers are washed with brine, 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 (1.3 g, 93%).

Workup

  1. customThe reaction is degassed with a flow of N2 for 30 min
  2. stirringstirred vigorously under open to the atmosphere for several hours
  3. customThe reaction 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-d4e844f33cee494781089d419b186604
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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