Imidazole → HCID 22878626, compound

HRID 352002Notes

Reaction equation

HRID 352002 reaction equation
[C:1]([C@@:3]1([N:34]2[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]2=[O:36])[O:33][C@H:7]([CH:8]([C:10]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[OH:9])[C@@H:5]([OH:6])[CH2:4]1)#[N:2].[C:43]([Si:47]([CH3:50])([CH3:49])Cl)([CH3:46])([CH3:45])[CH3:44].N1C=CN=C1>N1C=CC=CC=1>[C:1]([C@@:3]1([N:34]2[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]2=[O:36])[O:33][C@H:7]([CH:8]([C:10]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[OH:9])[C@@:5]([Si:47]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:50])[CH3:49])([OH:6])[CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 54519329HCID 54519329, compound

Product 1

HCID 22878626HCID 22878626, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

1′-Cyano-5′-(4,4′-dimethoxytrityl)thymidine in anhydrous pyridine is added to a stirred solution of t-butyldimethylchlorosilane (1.5 equivalents) and imidazole (3.0 equivalents) in anhydrous pyridine at 0° C. The resulting reaction mixture is stirred at room temperature overnight. Pyridine is evaporated and the residue dissolved in ethyl acetate, washed with brine. The crude is directly used for the next reaction.

Workup

  1. customThe resulting reaction mixture
  2. customPyridine is evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with brine
  5. customThe crude is directly used for the next reaction

Sources & evidence

ORD record
ord-ae53bcb2af1142f6a29a4bbd291a8c07
Source dataset
uspto-grants-2004_06
Patent number
US06743902B1

Reaction notes

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