Xanthine → 1,3-Dimethyl-7-(6-hydroxyhexyl)-xanthine

HRID 482882

Reaction equation

HRID 482882 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br)[CH:8]=[N:7][C:6]=2[N:5]([CH3:20])[C:3]1=[O:4].C([O-])(=[O:23])C.[K+].N1C(=O)C2NC=NC=2NC1=O.[I-].[K+]>C(OC(=O)C)(=O)C.C(O)(=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:23])[CH:8]=[N:7][C:6]=2[N:5]([CH3:20])[C:3]1=[O:4]

Participants

7

Reactant 4

HCID 1188XanthineHCID 4875Potassium IodideHCID 517044Potassium AcetateHCID 202440737-(6-Bromohexyl)-1,3-dimethylxanthine

Product 1

HCID 108027041,3-Dimethyl-7-(6-hydroxyhexyl)-xanthine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

1,3-dimethyl-7-(6-bromohexyl)-xanthine is refluxed overnight with a sixfold molar excess of potassium acetate with the addition of catalytic quantities, such as 2 mol percent, referred to the xanthine, of potassium iodide in a mixture of 5 ml of acetic anhydride and 200 ml of glacial acetic acid. The solvent is evaporated in vacuo. The residue is dissolved in water and the pH of the solution is adjusted to a value of 7 with 4N sodium hydroxide. The solution is then extracted with chloroform. The isolated 1,3-dimethyl-7-(acetoxyhexyl)-xanthine is subsequently hydrolysed to the corresponding hydroxyalkyl compound by boiling with 5% sulfuric acid.

Workup

  1. additionwith the addition of catalytic quantities
  2. customThe solvent is evaporated in vacuo
  3. dissolutionThe residue is dissolved in water
  4. extractionThe solution is then extracted with chloroform

Sources & evidence

ORD record
ord-e571a2eb32c64f79b711437d06908a8a
Source dataset
uspto-grants-1986_03
Patent number
US04576947

Linked notes

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