Imidazole → HCID 54193368, compound

HRID 2212808Notes

Reaction equation

HRID 2212808 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].N1C=CN=C1.[C:23]([Si:27]([CH3:30])([CH3:29])Cl)([CH3:26])([CH3:25])[CH3:24]>CN(C)C=O>[Si:27]([CH:7]([OH:8])[C@H:6]1[O:9][C@@H:1]([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@H:2]([OH:3])[C@@H:4]1[OH:5])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6029UridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 54193368HCID 54193368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 1 gram of uridine in 20 ml dry N, N-dimethylformamide is added 2.4 molar equivalents of imidazole followed by 1.2 molar equivalents of t-butyldimethylchlorosilane. The mixture is stirred with protection from moisture at room temperature for 20 hours, at which time the solvent is removed at 50° C. in vacuo. The residue is dissolved in 15 ml of ethyl acetate, the solution is washed with 10 ml of water, and the extract is dried with magnesium sulfate and evaporated to give a syrup. Crystallization from 10 ml of hot chloroform, to which is added hexane to the point of opalescence, followed by slow cooling to room temperature, gives 5′-(t-butyldimethylsilyl) uridine.

Workup

  1. customis removed at 50° C. in vacuo
  2. dissolutionThe residue is dissolved in 15 ml of ethyl acetate
  3. washthe solution is washed with 10 ml of water
  4. dry with materialthe extract is dried with magnesium sulfate
  5. customevaporated
  6. customto give a syrup
  7. customCrystallization from 10 ml of hot chloroform
  8. additionto which is added hexane to the point of opalescence
  9. temperatureby slow cooling to room temperature

Sources & evidence

ORD record
ord-d7298e7f499c490d85884a4b068bea87
Source dataset
uspto-grants-2006_09
Patent number
US07105498B2

Reaction notes

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