Methyl iodide → HCID 86752840, compound

HRID 964920Notes

Reaction equation

HRID 964920 reaction equation
[Mg].[CH3:2]I.[C:4]([C:7]1[C:8]([Cl:16])=[N:9][C:10]([CH:13]([F:15])[F:14])=[N:11][CH:12]=1)(=[O:6])[CH3:5].[Cl-].[NH4+]>C(OCC)C>[Cl:16][C:8]1[C:7]([C:4]([OH:6])([CH3:2])[CH3:5])=[CH:12][N:11]=[C:10]([CH:13]([F:15])[F:14])[N:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 19074103HCID 19074103, compound

Product 1

HCID 86752840HCID 86752840, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 470 mg of magnesium and 5 ml of dry ethyl ether, a solution of 2.76 g of methyl iodide dissolved in 15 ml of dry ethyl ether was added dropwise while the reaction mixture was kept under control so as to be refluxed moderately. After the dropwise addition, it was further refluxed for 45 minutes. The reaction mixture was allowed to cool to room temperature, then, 2 g of 5-acetyl-4-chlorodifluoromethylpyrimidine was quickly added dropwise thereto, and the reaction mixture was refluxed for another 1 hour. The reaction mixture was cooled with ice, and stirred while a saturated aqueous solution of ammonium chloride was added thereto. The ether layer was separated by decantation and washed with saturated aqueous salt solution three times in a separatory funnel. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting crude product was subjected to preparatory thin-layer chromatography (developing solvent: chloroform) three times, and as a result, 131 mg of the desired product was obtained as a viscous liquid. nD20.6 1.4982

Workup

  1. additionwas added dropwise while the reaction mixture
  2. temperatureto be refluxed moderately
  3. additionAfter the dropwise addition, it
  4. temperaturewas further refluxed for 45 minutes
  5. temperaturethe reaction mixture was refluxed for another 1 hour
  6. temperatureThe reaction mixture was cooled with ice
  7. additionwas added
  8. customThe ether layer was separated by decantation
  9. washwashed with saturated aqueous salt solution three times in a separatory funnel
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-89198d37c1444cd18adf609adf6c5bd9
Source dataset
uspto-grants-1998_06
Patent number
US05773388

Reaction notes

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