Methyl iodide → HCID 22417671, compound

HRID 1720369Notes

Reaction equation

HRID 1720369 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([C:19]#[N:20])=[N:16][C:17]=1[CH3:18].[CH3:21]N(C)P(=O)(N(C)C)N(C)C.CI.[NH4+].[Cl-]>C1COCC1>[CH2:11]([C:12]1[CH:13]=[CH:14][C:15]([C:19]#[N:20])=[N:16][C:17]=1[CH3:18])[CH3:21]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 224176635,6-Dimethylpyridine-2-carbonitrile

Product 1

HCID 22417671HCID 22417671, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium bis(trimethylsilyl)amide (41 mL, 0.5M in toluene, 20.4 mmol) was added to a solution of 2-cyano-5,6-dimethylpyridine from Example 1, Step 2 (2.45 g, 18.5 mmol) and hexamethylphosphoric triamide (9.7 mL, 55.6 mmol) in dry THF (30 mL) at -78° C. After stirring 30 minutes, MeI (5.77 mL, 92.7 mmol) was added and the reaction mixture stirred 45 minutes at -78° C. Saturated aq. NH4Cl was added, the mixture was extracted with EtOAc (3×), the organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (from 15:15:70 to 20:20:60 of Et2O: CH2Cl2 : hexanes) to give 1.2 g (44%) of the title compound.

Workup

  1. stirringthe reaction mixture stirred 45 minutes at -78° C
  2. extractionthe mixture was extracted with EtOAc (3×)
  3. dry with materialthe organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (from 15:15:70 to 20:20:60 of Et2O: CH2Cl2 : hexanes)

Sources & evidence

ORD record
ord-79804bdbd10e4dc3bd1cc11adf76b988
Source dataset
uspto-grants-1996_04
Patent number
US05506227

Reaction notes

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