Imidazole → 3'-O-t-butyldimethylsilyl-5'-iodo-5'-deoxythymidine

HRID 1489360Notes

Reaction equation

HRID 1489360 reaction equation
[I-:1].[C@@H:2]1([N:10]2[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7]O)[C@@H:4]([OH:5])[CH2:3]1.N1C=CN=C1.[C:24]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C.C(OCC)(=O)C>[Si:28]([O:5][C@@H:4]1[C@@H:6]([CH2:7][I:1])[O:9][C@@H:2]([N:10]2[CH:18]=[C:16]([CH3:17])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:3]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 131720246Thymidine iodide

Product 1

HCID 103898023'-O-t-butyldimethylsilyl-5'-iodo-5'-deoxythymidineYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the thymidine iodide (8.0 g, 24.7 mmol) prepared according to the method of Example 24 in dry DMF, was added imidazole (4.2 g, 61.7 mmol). After 5 minutes tert-butyldimethyl silyl chloride (4.47 g, 29.64 mmol) was added and the mixture stirred for 4 hours. The reaction mixture was then diluted with ethyl acetate (250 ml), washed with water (2×100 ml) and brine (50 ml) and then dried with sodium sulfate. The title compound was purified by flash chromatography using 60% ethyl acetate in hexane in 92% yield.

Workup

  1. washwashed with water (2×100 ml) and brine (50 ml)
  2. dry with materialdried with sodium sulfate
  3. customThe title compound was purified by flash chromatography

Sources & evidence

ORD record
ord-aae190b5018c4a78b0157ce3b1b8e038
Source dataset
uspto-grants-1997_10
Patent number
US05677439

Reaction notes

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