Water → 7-Benzyloxymethyl-3,7-dihydro-6-methylthio-3-n-propyl-2H-purin-2-one

HRID 1681631Notes

Reaction equation

HRID 1681631 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+].Cl[CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C>[CH2:21]([O:20][CH2:19][N:5]1[C:4]2[C:3]([S:2][CH3:1])=[N:11][C:10](=[O:12])[N:9]([CH2:13][CH2:14][CH3:15])[C:8]=2[N:7]=[CH:6]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 104436123,7-Dihydro-6-methylthio-3-n-propyl-2H-purin-2-one

Product 1

HCID 198053877-Benzyloxymethyl-3,7-dihydro-6-methylthio-3-n-propyl-2H-purin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 224 mg (1.0 mmol) of Compound b obtained in Reference Example 2 was dissolved in 2 ml of N,N'-dimethylformamide, 48.0 mg (1.2 mmol) of 60% sodium hydride was added to the mixture under ice cooling. 15 minutes after, 209 μl (1.5 mmol) of benzyl chloromethyl ether was added to the mixture. The mixture was stirred for an hour, poured onto 10 ml of water, and extracted 3 times with 5 ml of chloroform. After washing with a saturated aqueous sodium chloride solution, the extracts were dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated with ether to give 223 mg (yield, 65%) of Compound f as a white powder.

Workup

  1. extractionextracted 3 times with 5 ml of chloroform
  2. washAfter washing with a saturated aqueous sodium chloride solution
  3. dry with materialthe extracts were dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated with ether
  6. customto give

Sources & evidence

ORD record
ord-e2622df06ca34a469e423314ff8ee197
Source dataset
uspto-grants-1992_12
Patent number
US05173492

Reaction notes

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