Imidazole → 5'-O-TBDMS-N2-ibu-dG

HRID 968365Notes

Reaction equation

HRID 968365 reaction equation
[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:24])[C:10]2[N:11]=[CH:12][N:13]([C:22]=2[N:23]=1)[C@@H:14]1[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[CH2:15]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].N1C=CN=C1.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>CN(C=O)C>[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:24])[C:10]2[N:11]=[CH:12][N:13]([C:22]=2[N:23]=1)[C@@H:14]1[O:21][C@H:18]([CH2:19][O:20][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C@@H:16]([OH:17])[CH2:15]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 135407017Guanosine, 2'-deoxy-N-(2-methyl-1-oxopropyl)-

Product 1

HCID 1359094375'-O-TBDMS-N2-ibu-dGYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N2-isobutyryl-2′-deoxyguanosine (20.5 g) was dissolved in 200 ml of DMF. After 18.5 g of imidazole was dissolved in the resultant solution by addition, 21.4 g of tert-butyldimethylsilyl chloride was then added. DMF (100 ml) was further added and the solution was stirred at room temperature. After 8 hours, extraction using chloroform was carried out and the organic layer was washed by a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After concentration of the extract, the target compound was separated by column chromatography (methanol/chloroform). The fraction solution including the target compound was prepared and concentrated to obtain 20.5 g of the titled compound (yield; 74%).

Workup

  1. additionwas then added
  2. extractionextraction
  3. washthe organic layer was washed by a saturated aqueous solution of sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customAfter concentration of the extract, the target compound was separated by column chromatography (methanol/chloroform)
  6. customwas prepared
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf20ec1903774fca8e57def2cb36b186
Source dataset
uspto-grants-2005_10
Patent number
US06958391B2

Reaction notes

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