Methyl iodide → 1H-Purine-2,6-dione, 3,7-dihydro-1,3-diethyl-8-(2-(3-methoxyphenyl)ethenyl)-7-methyl-, (E)-

HRID 1379000Notes

Reaction equation

HRID 1379000 reaction equation
[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[NH:10][C:9](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)=[N:8][C:7]=2[N:6]([CH2:24][CH3:25])[C:4]1=[O:5])[CH3:2].[C:26](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[N:10]([CH3:26])[C:9](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)=[N:8][C:7]=2[N:6]([CH2:24][CH3:25])[C:4]1=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 64488781H-Purine-2,6-dione, 3,7-dihydro-1,3-diethyl-8-(2-(3-methoxyphenyl)ethenyl)-, (E)-

Product 1

HCID 64488791H-Purine-2,6-dione, 3,7-dihydro-1,3-diethyl-8-(2-(3-methoxyphenyl)ethenyl)-7-methyl-, (E)-Yield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Compound r (1.70 g, 5.0 mmol) obtained in Reference Example 17 was dissolved in 40 ml of dimethylformamide. To the solution were added 1.73 g (12.5 mmol) of potassium carbonate and subsequently 0.62 ml (10.0 mmol) of methyl iodide, and the resulting mixture was stirred at 50° C. for 30 minutes. After cooling, insoluble matters were filtered off, and 100 ml of water was added to the filtrate. The mixture was extracted three times with 50 ml of chloroform. The extract was washed twice with water and once with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The obtained crude crystals were purified by silica gel column chromatography (eluent: 40% ethyl acetate/hexane), followed by recrystallization from cyclohexane/toluene to give 1.10 g (yield 62%) of Compound s as pale yellow needles.

Workup

  1. temperatureAfter cooling
  2. filtrationinsoluble matters were filtered off
  3. addition100 ml of water was added to the filtrate
  4. extractionThe mixture was extracted three times with 50 ml of chloroform
  5. washThe extract was washed twice with water and once with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customfollowed by evaporation under reduced pressure
  8. customThe obtained crude crystals
  9. customwere purified by silica gel column chromatography (eluent: 40% ethyl acetate/hexane)
  10. customfollowed by recrystallization from cyclohexane/toluene

Sources & evidence

ORD record
ord-68f9e4c7f750414ca834a046c99cedf4
Source dataset
uspto-grants-1997_09
Patent number
US05670498

Reaction notes

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