Dimethylformamide → HCID 15462524, compound

HRID 842071Notes

Reaction equation

HRID 842071 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:7])[CH:5]=[O:6].O=C1NC2[C:11](=[N:12][C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][CH:15]=2)[N:10]1[CH2:24][C:25]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:26].CI>C(Cl)(Cl)Cl.O>[CH3:3][N:4]1[C:7]2[C:11](=[N:12][C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][CH:15]=2)[N:10]([CH2:24][C:25]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:26])[C:5]1=[O:6]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15462523HCID 15462523, compound

Product 1

HCID 15462524HCID 15462524, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of about 60% sodium hydride (oily) (0.8 g) and dimethylformamide (50 ml) is added 7,8-dihydro-8-oxo-2-phenyl-N,N-dipropyl-9H-purin-9-acetamide (6 g) obtained in Example 79 in portions at 0-5° C., and the mixture is stirred at 0° C. for one hour. To the mixture is added dropwise methyl iodide (2.9 g) at the same temperature. After the addition, the mixture is stirred at room temperature for two hours. To the reaction mixture are added water and chloroform, and the chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from ethanol to give the desired compound (6 g).

Workup

  1. additionAfter the addition
  2. stirringthe mixture is stirred at room temperature for two hours
  3. customthe chloroform layer is separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5b4431e9e5e34f5a87745a1ede813824
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

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