Water → Purine-2,6(1H,3H)-dione, 7-(2-bromobenzyl)-8-chloro-1,3-dimethyl-

HRID 984821Notes

Reaction equation

HRID 984821 reaction equation
[Cl:1][C:2]1[NH:11][C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Br.CCOC(C)=O.O>CN(C=O)C.CCN(C(C)C)C(C)C>[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][N:11]1[C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=[C:2]1[Cl:1]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 106618-ChlorotheophyllineHCID 769652-Bromobenzyl bromide

Product 1

HCID 598207Purine-2,6(1H,3H)-dione, 7-(2-bromobenzyl)-8-chloro-1,3-dimethyl-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
65 °C

Procedure

8-Chlorotheophylline (10 g, 46.6 mmol) was dissolved in 250 ml of DMF and 8 ml of DIEA, and 2-bromobenzyl bromide (12.2 g, 48.9 mmol) was added. The mixture was stirred at 65° C. for 2 hours. The reaction mixture was added 20 ml of EtOAc and 250 ml of cold water. The white precipitate was collected by filtration to afford compound (10A) as white crystals.

Workup

  1. filtrationThe white precipitate was collected by filtration

Sources & evidence

ORD record
ord-98380369814345b6b4dbb6783dc7d6e3
Source dataset
uspto-grants-2005_03
Patent number
US06869947B2

Reaction notes

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