Sodium hydride → 3,7-Dihydro-3,7-di-n-propyl-6-methylthio-2H-purin-2-one

HRID 1681632Notes

Reaction equation

HRID 1681632 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[NH:5][CH:6]=[N:7][C:8]=2[N:9]([CH2:13][CH2:14][CH3:15])[C:10](=[O:12])[N:11]=1.[H-].[Na+].[CH2:18](I)[CH2:19][CH3:20].[Cl-].[NH4+]>CN(C)C=O>[CH2:13]([N:9]1[C:8]2[N:7]=[CH:6][N:5]([CH2:18][CH2:19][CH3:20])[C:4]=2[C:3]([S:2][CH3:1])=[N:11][C:10]1=[O:12])[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 336431-IodopropaneHCID 104436123,7-Dihydro-6-methylthio-3-n-propyl-2H-purin-2-one

Product 1

HCID 198054043,7-Dihydro-3,7-di-n-propyl-6-methylthio-2H-purin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.00 g (8.93 mmol) of Compound b obtained in Reference Example 2 was gently added to a suspension of 356 mg (8.93 mmol) of 60% sodium hydride in 20 ml of N,N-dimethylformamide at 0° C. 10 minutes after, 2.64 ml (27.0 mmol) of propyl iodide was gently added to the mixture. The mixture was stirred at room temperature for 2 hours and a half. After 150 ml of saturated ammonium chloride aqueous solution was added to the reaction solution, the mixture was extracted 3 times with chloroform. The extracts were combined and washed twice with a saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. 50% ether/n-hexane was added to the residue. The precipitates were taken out by filtration to give 2.09 g (yield, 84%) of Compound o as a light yellow powder.

Workup

  1. extractionthe mixture was extracted 3 times with chloroform
  2. washwashed twice with a saturated aqueous sodium chloride
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. addition50% ether/n-hexane was added to the residue
  6. filtrationThe precipitates were taken out by filtration
  7. customto give

Sources & evidence

ORD record
ord-5bb922fd3d40432c9d65227ba574e00e
Source dataset
uspto-grants-1992_12
Patent number
US05173492

Reaction notes

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