1,2-Dimethoxyethane → 1,3-Dimethyl-7-(5,6-dihydroxyhexyl)xanthine

HRID 986472Notes

Reaction equation

HRID 986472 reaction equation
Cl(O)(=O)(=O)=O.[CH3:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH:22]3[O:24][CH2:23]3)[CH:13]=[N:12][C:11]=2[N:10]([CH3:25])[C:8]1=[O:9].C[O:27]CCOC.C(=O)(O)[O-].[Na+]>O>[CH3:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([OH:24])[CH2:23][OH:27])[CH:13]=[N:12][C:11]=2[N:10]([CH3:25])[C:8]1=[O:9]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 131516391,3-Dimethyl-7-(5,6-epoxyhexyl)xanthine

Product 1

HCID 131516061,3-Dimethyl-7-(5,6-dihydroxyhexyl)xanthine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.24 ml of perchloric acid (70% strength) was added dropwise with stirring in 5 minutes to a solution of 3.6 g of 1,3-dimethyl-7-(5,6-epoxyhexyl)xanthine in 280 ml of a mixture of ethylene glycol dimethyl ether and water (volume ratio 3:2) at room temperature. After stirring at room temperature for 16 hours, the mixture was neutralized with sodium bicarbonate solution and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (mobile phase: chloroform/ethanol, volume ratio 8/2) and recrystallization from ethyl acetate.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (mobile phase: chloroform/ethanol, volume ratio 8/2) and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-08b7b3c0bdd04219864615adfe7fe42d
Source dataset
uspto-grants-1987_12
Patent number
US04713455

Reaction notes

Loading…