Imidazole → 5'-O-tert-butyldimethylsilyl-5-trifluoromethyl-2'-deoxyuridine

HRID 37063Notes

Reaction equation

HRID 37063 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1.N1C=CN=C1.[C:26]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O.C(Cl)(Cl)Cl.CO>[Si:30]([O:14][CH2:13][C@H:12]1[O:15][C@@H:8]([N:7]2[CH:16]=[C:3]([C:2]([F:1])([F:19])[F:20])[C:4](=[O:18])[NH:5][C:6]2=[O:17])[CH2:9][C@@H:10]1[OH:11])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 6256TrifluridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 100929765'-O-tert-butyldimethylsilyl-5-trifluoromethyl-2'-deoxyuridineYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

A 1.0 g quantity of 5-trifluoromethyl-2'-deoxyuridine (3.6 mmoles) was dissolved in 3 ml of N,N-dimethylformamide. To the solution were added 0.49 g (7.2 mmoles) of imidazole and 0.64 g (4.3 mmoles) of tertbutyldimethylsilyl chloride, and the reaction was conducted at room temperature for 10 hours. The reaction mixture was treated in the same manner as in Example 1 with the exception of using chloroform/methanol (30:1) as an eluent for silica gel column chromatography, giving 0.6 g of the title compound as white crystals having a melting point of 199° to 200° C. Yield: 41%.

Sources & evidence

ORD record
ord-1ba6f30e44d647b58a6d608c0cc4e907
Source dataset
uspto-grants-1995_05
Patent number
US05420117

Reaction notes

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