Theophylline → 7-[2-Hydroxy-3-(5-methyl-1,2,4-oxadiazol-3-yl)-propan-1-yl]-theophylline

HRID 1285174Notes

Reaction equation

HRID 1285174 reaction equation
[O:1]1[CH2:10][CH:2]1[CH2:3][C:4]1[N:8]=[C:7]([CH3:9])[O:6][N:5]=1.[N:11]1([C:22](=[O:23])[C:21]2[NH:20][CH:19]=[N:18][C:17]=2[N:15]([CH3:16])[C:13]1=[O:14])[CH3:12]>C(O)(C)C.N1C=CC=CC=1>[OH:1][CH:2]([CH2:3][C:4]1[N:8]=[C:7]([CH3:9])[O:6][N:5]=1)[CH2:10][N:20]1[C:21]2[C:22](=[O:23])[N:11]([CH3:12])[C:13](=[O:14])[N:15]([CH3:16])[C:17]=2[N:18]=[CH:19]1

Participants

5

Reactant 2

HCID 2153TheophyllineHCID 202499715-Methyl-3-[(oxiran-2-yl)methyl]-1,2,4-oxadiazole

Product 1

HCID 202499677-[2-Hydroxy-3-(5-methyl-1,2,4-oxadiazol-3-yl)-propan-1-yl]-theophyllineYield 86%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3776IsopropanolSolvent

Procedure

1.4 g. 3-(2,3-epoxy-propyl)-5-methyl-1,2,4-oxadiazole and 1.8 g. of theophylline are boiled under stirring in a mixture of 20 cm3 isopropyl alcohol and 0.1 cm3 of pyridine for 8 hours. 2.75 g. (86% yield) of 7-[2-hydroxy-3-(5-methyl-1,2,4-oxadiazol-3-yl)-propan-1-yl]-theophylline are obtained.

Sources & evidence

ORD record
ord-1704eb37189c489a88344f9539f22e86
Source dataset
uspto-grants-1986_01
Patent number
US04565817

Reaction notes

Loading…