Imidazole → HCID 22878626, compound

HRID 727469Notes

Reaction equation

HRID 727469 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-5cb97395f9864ccf80a2556dad912d42
Source dataset
uspto-grants-1998_01
Patent number
US05712378

Reaction notes

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