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

HRID 2290246Notes

Reaction equation

HRID 2290246 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-0768ee77b848430ebe2d343af2d973af
Source dataset
uspto-grants-1986_10
Patent number
US04616020

Reaction notes

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