Theophylline → 7-(3-Bromopropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione

HRID 986747Notes

Reaction equation

HRID 986747 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[Br:14][CH2:15][CH2:16][CH2:17]Br.C(N(CC)CC)C>CN(C)C=O>[Br:14][CH2:15][CH2:16][CH2:17][N:10]1[C:11]2[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=2[N:8]=[CH:9]1

Participants

5

Reactant 3

HCID 2153TheophyllineHCID 80011,3-DibromopropaneHCID 8471Triethylamine

Product 1

HCID 900187-(3-Bromopropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dioneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of theophylline (10.0 g, 0.0555 mol), 1,3-dibromopropane (11.6 ml, 23.1 g, 0.114 mol) and triethylamine (10.5 ml, 7.62 g, 0.0753 mol) in N,N-dimethylformamide (250 ml) was stirred at 60° C. overnight. The stirring was continued one day at room temperature. The solvent was evaporated under reduced pressure. The residue was suspended in CH2Cl2 and water. An emulsion was caused by a fine solid suspended in the mixture. The solid was filtered out and discarded. The aqueous layer was extracted three times with CHCl3. The combined organic layers were dried with MgSO4. Evaporation of the solvent under reduced pressure gave 7-(3-bromopropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione (12.8 g, 77% yield).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationThe solid was filtered out and
  3. extractionThe aqueous layer was extracted three times with CHCl3
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7bc150b89e6e4fff8b0ee06d106e3d5b
Source dataset
uspto-grants-1987_12
Patent number
US04716166

Reaction notes

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