N9-phenethyl-8-bromomethyladenine → N9-phenethyl-8-diethylphosphonomethoxymethyladenine

HRID 1181201Notes

Reaction equation

HRID 1181201 reaction equation
[CH2:1]([N:9]1[C:17]([CH2:18]Br)=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:20])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Na].[OH:22][CH2:23][P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27]>CN(C=O)C>[CH2:1]([N:9]1[C:17]([CH2:18][O:22][CH2:23][P:24]([O:28][CH2:29][CH3:30])([O:25][CH2:26][CH3:27])=[O:31])=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:20])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 42637845N9-phenethyl-8-bromomethyladenineHCID 86585098Diethyl hydroxymethylphosphonate sodium salt

Product 1

HCID 42637083N9-phenethyl-8-diethylphosphonomethoxymethyladenine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N9-phenethyl-8-bromomethyladenine (1 mmol) in DMF was treated with a solution of diethyl hydroxymethylphosphonate sodium salt (1 mmol) in DMF at 25° C. for 1 h. Extraction and chromatography gave N9-phenethyl-8-diethylphosphonomethoxymethyladenine as a white solid. TLC: Rf=0.31, 10% MeOH—CH2Cl2.

Workup

  1. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-f5f1d6e621cc40db8bf32fdae432bb69
Source dataset
uspto-grants-2007_10
Patent number
US07285543B2

Reaction notes

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