Imidazole → HCID 11532876, compound

HRID 1818667Notes

Reaction equation

HRID 1818667 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1.[Si:17](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CN=C1>CN(C=O)C>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 1624502',3'-Dideoxy-3'-fluorouridine

Product 1

HCID 11532876HCID 11532876, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesised following a similar procedure as described for Example 12. 3′-Fluoro-2′,3′-dideoxyuridine (0.176 g, 0.77 mmol) was reacted with tert-butyldiphenylsilyl chloride (0.238 g, 0.87 mmol) and imidazole (0.116 g, 1.70 mmol) in dry DMF (4 mL) for 3 h. Compound WSP948 was obtained as a white solid (0.331 g, 92%).

Sources & evidence

ORD record
ord-393c512424434781b5b454507aff1c69
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

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