Ethanol → 7-(4-(4-Chlorobenzoyl)benzyl)-2,6-diethoxypurine

HRID 1291205Notes

Reaction equation

HRID 1291205 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][N:13]3[C:21]4[C:16](=[N:17][C:18](Cl)=[N:19][C:20]=4Cl)[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[O-:28][CH2:29][CH3:30].[Na+].[CH2:32]([OH:34])[CH3:33]>O>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][N:13]3[C:21]4[C:16](=[N:17][C:18]([O:34][CH2:32][CH3:33])=[N:19][C:20]=4[O:28][CH2:29][CH3:30])[N:15]=[CH:14]3)=[CH:24][CH:25]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 189188407-(4-(4-Chlorobenzoyl)benzyl)-2,6-dichloropurine

Product 1

HCID 189189697-(4-(4-Chlorobenzoyl)benzyl)-2,6-diethoxypurineYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 7-(4-(4-chlorobenzoyl)benzyl)-2,6-dichloropurine (1.12 g) in ethanol (30 ml) was added sodium ethoxide (1.83 g) and the mixture was stirred at room temperature for 96 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was washed with ether and hexane to provide the title compound (0.78 g, 67%) as colorless powder. 1H-NMR (CDCl3) δ: 1.34(3H,t,J=7.OHz), 1.50(3H,t,J=7.OHz), 4.50(2H,q,J=7.OHz), 4.55(2H,q,J=7.OHz), 5.53(2H,s), 7.25-7.80(8H,m), 7.98(1H,s).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. washThe residue was washed with ether and hexane

Sources & evidence

ORD record
ord-9e8f4277d9f64b7f9d09d65a429406a6
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…