Chlorosuccinimide → 1-(4-Hydroxy-3-(hydroxymethyl)-1-butyl)-5-(1-azido-2-chloroethyl)uracil

HRID 732924Notes

Reaction equation

HRID 732924 reaction equation
[Cl:1]N1C(=O)CCC1=O.[OH:9][CH2:10][CH:11]([CH2:24][OH:25])[CH2:12][CH2:13][N:14]1[CH:21]=[C:20]([CH:22]=[CH2:23])[C:18](=[O:19])[NH:17][C:15]1=[O:16].[N-:26]=[N+:27]=[N-:28].[Na+]>COCCOC.O>[OH:9][CH2:10][CH:11]([CH2:24][OH:25])[CH2:12][CH2:13][N:14]1[CH:21]=[C:20]([CH:22]([N:26]=[N+:27]=[N-:28])[CH2:23][Cl:1])[C:18](=[O:19])[NH:17][C:15]1=[O:16]

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 33557Sodium AzideHCID 100372831-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-5-vinyluracil

Product 1

HCID 4903871-(4-Hydroxy-3-(hydroxymethyl)-1-butyl)-5-(1-azido-2-chloroethyl)uracilYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-5 °C

Procedure

N-Chlorosuccinimide (50 mg, 0.37 mmol) was added slowly with stirring to a precooled (−5° C.) suspension, prepared by mixing a solution of 20 (75 mg, 0.31 mmol) in 1,2-dimethoxyethane (25 ml) with a solution of sodium azide (81 mg, 1.24 mmol) in water (0.23 ml). The reaction mixture was allowed to proceed for 2 h at 0° C. with stirring and the solvent was removed in vacuo. The resulting residue was purified by silica gel column chromatography using chloroform:methanol (90:10, v/v) as eluent to afford 21b (46 mg, 47%) as a viscous oil.

Workup

  1. customprepared
  2. stirringwith stirring
  3. customthe solvent was removed in vacuo
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3a5e5be6bbd44d73bed28cafe5fbe21a
Source dataset
uspto-grants-2009_09
Patent number
US07589077B2

Reaction notes

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