Methyl iodide → HCID 18662973, compound

HRID 1956180Notes

Reaction equation

HRID 1956180 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:22])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1([C:14]1[C:15]([S:20][CH3:21])=[N:16][CH:17]=[N:18][CH:19]=1)[OH:13].[H][H].[CH3:25]I>O1CCCC1.O>[CH3:3][C:4]1([CH3:22])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1([C:14]1[C:15]([S:20][CH3:21])=[N:16][CH:17]=[N:18][CH:19]=1)[O:13][CH3:25]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23227014HCID 23227014, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18662973HCID 18662973, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.16 g of 60 percent in mineral oil, 4.0 mmol) was added with stirring to a solution of 1.0 g (3.5 mmol) of 5-(2,2-dimethyl-1-hydroxyindan-1-yl)-4-(methylthio)pyrimidine in 10 mL of tetrahydrofuran. After the hydrogen evolution and exotherm were complete, 0.43 g (3 mmol) of methyl iodide was added and the mixture was allowed to react overnight at ambient temperature. The mixture was then poured into 20 mL of cold water and the resulting mixture was extracted with ethyl acetate. The organic extract was washed with water and then with concentrated aqueous sodium hydroxide, was dried over magnesium sulfate, and was concentrated by evaporation under reduced pressure. The oily solid residue was extracted with hexane to remove cold hexane insolubles and then hot hexane insolubles were removed by filtration of a hot hexane solution. The hexane was removed from the filtrate by evaporation under reduced pressure to obtain 0.87 g of the title compound as a white solid melting at 130°-132° C.

Workup

  1. customto react overnight at ambient temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialwith concentrated aqueous sodium hydroxide, was dried over magnesium sulfate
  6. concentrationwas concentrated by evaporation under reduced pressure
  7. extractionThe oily solid residue was extracted with hexane
  8. customto remove cold hexane insolubles
  9. customhot hexane insolubles were removed by filtration of a hot hexane solution
  10. customThe hexane was removed from the filtrate by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b06cedfe34894138bedcc30bd5ca3847
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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