Trifluoroacetic acid → HCID 69867178, compound

HRID 1791997Notes

Reaction equation

HRID 1791997 reaction equation
Cl[C:2]1[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:9]2[C:8](=[O:16])[NH:7][C:6](=[O:17])[N:5]([CH3:18])[C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(OC([N:39]1[CH2:45][CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)=O)(C)(C)C.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>CN(C)C=O.C(OCC)(=O)C.O>[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[CH2:30]([O:29][C:27](=[O:28])[CH2:26][N:7]1[C:8](=[O:16])[C:9]2[N:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:2]([N:39]3[CH2:45][CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)=[N:3][C:4]=2[N:5]([CH3:18])[C:6]1=[O:17])[CH3:31]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12183Ethyl iodoacetateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 220297223-Methyl-7-(3-methyl-2-buten-1-yl)-8-chloro-xanthine

Product 1

HCID 69867178HCID 69867178, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

8-Chloro-3-methyl-7-(3-methylbut-2-enyl)-3,7-dihydropurine-2,6-dione (100 mg) and potassium carbonate (103 mg) were suspended in N,N-dimethylformamide (2 ml), ethyl iodoacetate (66 μl) was added thereto, and the mixture was stirred at 120° C. for 2 hours and 30 minutes. The reaction mixture was diluted with ethyl acetate and water, extracted with ethyl acetate, and after washing with water the solvent was removed by distillaion at reduced pressure from the organic layer to give a brown solid. The resulting brown solid (30 mg) and 1-homopiperazine carboxylic acid tert-butyl ester (49 μl) were stirred at 140° C. for 1 hour, then trifluoroacetic acid (0.5 ml) was added thereto, and the reaction mixture was stirred at room temperature for 30 minutes. After removing the solvent by distillation at reduced pressure from the reaction mixture, the residue was purified by HPLC with a reversed phase column using water-acetonitrile-trifluoroacetic acid system as eluent to give 21.2 mg of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washafter washing with water the solvent
  3. customwas removed by distillaion at reduced pressure from the organic layer
  4. customto give a brown solid
  5. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  6. customAfter removing the solvent
  7. distillationby distillation at reduced pressure from the reaction mixture
  8. customthe residue was purified by HPLC with a reversed phase column

Sources & evidence

ORD record
ord-13ba33f836d54cd4a64ddcc47e367714
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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