Sodium Iodide → 2'-O-Pentyluridine

HRID 1416707Notes

Reaction equation

HRID 1416707 reaction equation
C([C@@:5]1([OH:26])[C@H:9]([O:10]CCCC)[C@@H:8]([C:15](=[SnH2])[OH:16])[O:7][C@H:6]1[N:18]1[CH:25]=[CH:24][C:22](=[O:23])[NH:21][C:19]1=[O:20])CCC.Br[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[I-].[Na+]>CN(C=O)C>[CH2:28]([O:26][C@@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:15][OH:16])[O:7][C@H:6]1[N:18]1[CH:25]=[CH:24][C:22](=[O:23])[NH:21][C:19]1=[O:20])[CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 80571-BromopentaneHCID 1317200902',3'-O-dibutylstannyleneuridine

Product 1

HCID 155460142'-O-Pentyluridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Utilizing the procedures of Examples 50 and 51, 2',3'-O-dibutylstannylene uridine (19.1 g) was treated with bromopentane (7 ml, 1.3 eq.) and sodium iodide (4.5 g) in DMF (90 ml). Purification on a silica gel column utilizing MeOH/CH2Cl2 5%→10% yielded the a mixture of 2' and 3' isomers of the product as a dark oil (9.8 g).

Workup

  1. customPurification on a silica gel column
  2. customyielded

Sources & evidence

ORD record
ord-e1ab0ee918d441bd8280500af7d77c0d
Source dataset
uspto-grants-1999_06
Patent number
US05914396

Reaction notes

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