Theophylline → 7-[2-(5-Methyl-1,2,4-oxadiazol-3-yl)-ethan-1-yl]-theophylline

HRID 1285172Notes

Reaction equation

HRID 1285172 reaction equation
[CH:1]([C:3]1[N:7]=[C:6]([CH3:8])[O:5][N:4]=1)=[CH2:2].[N:9]1([C:20](=[O:21])[C:19]2[NH:18][CH:17]=[N:16][C:15]=2[N:13]([CH3:14])[C:11]1=[O:12])[CH3:10]>CN(C)C=O>[CH3:8][C:6]1[O:5][N:4]=[C:3]([CH2:1][CH2:2][N:18]2[C:19]3[C:20](=[O:21])[N:9]([CH3:10])[C:11](=[O:12])[N:13]([CH3:14])[C:15]=3[N:16]=[CH:17]2)[N:7]=1

Participants

4

Reactant 2

HCID 2153TheophyllineHCID 125514583-Ethenyl-5-methyl-1,2,4-oxadiazole

Product 1

HCID 202499187-[2-(5-Methyl-1,2,4-oxadiazol-3-yl)-ethan-1-yl]-theophyllineYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.2 g. of 3-vinyl-5-methyl-1,2,4-oxadiazole, 30 cm3 dimethylformamide and 0.2 cm3Triton-B catalyst are boiled with 3.6 g. of theophylline for 1 hour. The solvent is distilled off and the residue is crystallized from ethanol. 4.2 g. (72% yield) of 7-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-ethan-1-yl]-theophylline are obtained. m.p.: 112°-114° C.

Workup

  1. distillationThe solvent is distilled off
  2. customthe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-5270524b2ee242a68e0e92835a4cd586
Source dataset
uspto-grants-1986_01
Patent number
US04565817

Reaction notes

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