Reaction #1909806

ord-2146565f51b14380b6ac1ae484262eaa

Reaction equation

Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n(COCc2ccccc2)c1=O
3-benzyloxymethyl-5-methyluridine
[H-].[Na+]
NaH
ClCCCCBr
1-Bromo-4-chlorobutane
→
Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCCCCl)c(=O)n(COCc2ccccc2)c1=O
title compound
Yield 41.0%
Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCCCCl)c(=O)n(COCc2ccccc2)c1=O
3-Benzyloxymethyl-5-methyl-2′-O-(4-chlorobutyl)uridine
Yield 41.0%

Reactants

Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n(COCc2ccccc2)c1=O
3-benzyloxymethyl-5-methyluridine
[H-].[Na+]
NaH
ClCCCCBr
1-Bromo-4-chlorobutane

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe reaction was then quenched (MeOH)
  2. 2
    Concentrationconcentrated in vacuo
  3. 3
    Otherthe residue chromatographed on silica gel CHCl3/MeOH 95/5

Procedure

A solution of 3-benzyloxymethyl-5-methyluridine (25.9 g, 68 mmol) was treated with NaH (60% oil, 7.9 g, 200 mmol) for 1 hr at room temp. 1-Bromo-4-chlorobutane (19.7 g, 115 mmol) was added slowly and the reaction stirred at room temp. for 16 hrs. The reaction was then quenched (MeOH), concentrated in vacuo and the residue chromatographed on silica gel CHCl3/MeOH 95/5 to give the title compound in 41% yield. 1H NMR (DMSO-d6) δ 5.87 (d, 1H, C1′H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07037646B1uspto-grants-2006_05