Methyl iodide → HCID 13824244, compound

HRID 1906850Notes

Reaction equation

HRID 1906850 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:9]=[N:10][N:11]2[C:16]([C:17]3[CH:18]=[C:19]([NH:23][C:24]([CH:26]4[CH2:28][CH2:27]4)=[O:25])[CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:14]=[N:13][C:12]=12)=[O:7].[H-].[Na+].[CH3:31]I>CN(C)C=O.C(O)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:9]=[N:10][N:11]2[C:16]([C:17]3[CH:18]=[C:19]([N:23]([CH3:31])[C:24]([CH:26]4[CH2:28][CH2:27]4)=[O:25])[CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:14]=[N:13][C:12]=12)=[O:7]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13824242HCID 13824242, compound

Product 1

HCID 13824244HCID 13824244, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

To a 3.85 g sample of N-[3-[3-(2-furanylcarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]cyclopropanecarboxamide in 40 ml of dimethylformamide is added 0.384 g of 60% sodium hydride in oil. The mixture is stirred at room temperature under argon for one hour and then 0.65 ml of methyl iodide is added. After stirring overnight at room temperature, several drops of acetic acid are added, the mixture poured onto ice-water and extracted with dichloromethane. The extracts are washed with water, dried over sodium sulfate and the solvent removed under reduced pressure. The residue is dissolved in dichloromethane, filtered through a short pad of hydrous magnesium silicate and the pad washed with dichloromethane. The filtrate is concentrated and hexane added. Cooling gives the desired product as crystals, mp 207°-209° C.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. additionthe mixture poured onto ice-water
  3. extractionextracted with dichloromethane
  4. washThe extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed under reduced pressure
  7. dissolutionThe residue is dissolved in dichloromethane
  8. filtrationfiltered through a short pad of hydrous magnesium silicate
  9. washthe pad washed with dichloromethane
  10. concentrationThe filtrate is concentrated
  11. additionhexane added
  12. temperatureCooling

Sources & evidence

ORD record
ord-8b16a9fefb754782bb7ea069a90fddef
Source dataset
uspto-grants-1987_03
Patent number
US04654347

Reaction notes

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