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Iodoethane → 7-Ethoxymethyl-1-ethyl-3-methylxanthine

HRID 1992
Notes
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Reaction equation

HRID 1992 reaction equation
[CH2:1]([O:3][CH2:4][N:5]1[C:13]2[C:12](=[O:14])[NH:11][C:10](=[O:15])[N:9]([CH3:16])[C:8]=2[N:7]=[CH:6]1)[CH3:2].[CH2:17](I)[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:17][CH3:18])[C:10](=[O:15])[N:9]([CH3:16])[C:8]=2[N:7]=[CH:6]1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 137476847-Ethoxymethyl-3-methylxanthine

Product 1

HCID 196891947-Ethoxymethyl-1-ethyl-3-methylxanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

30 g (0.134 mol) of 7-ethoxymethyl-3-methylxanthine were suspended in 500 ml of absolute DMF with 25 g (0.161 mol) of ethyl iodide and 22.2 g (0.161 mol) of potassium carbonate and the mixture was stirred at 70° C. for 5 hours. The solution was filtered and the residue which remained was crystallized in diisopropyl ether. 28.7 g (85% of theory) of the title substance were obtained and employed without purification in Example 4b).

Workup

  1. filtrationThe solution was filtered
  2. customthe residue which remained was crystallized in diisopropyl ether
  3. custom28.7 g (85% of theory) of the title substance were obtained
  4. customemployed without purification in Example 4b)

Sources & evidence

ORD record
ord-841b9089cd1f4520ba61b48f730e5eeb
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728686

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes