Imidazole → HCID 68699325, compound

HRID 1818662Notes

Reaction equation

HRID 1818662 reaction equation
N1C=CN=C1.[C@@H:6]1([N:14]2[CH:21]=[CH:20][C:18](=[O:19])[NH:17][C:15]2=[O:16])[O:13][C@H:10]([CH2:11][OH:12])[C@@H:8]([OH:9])[CH2:7]1.[CH:22]([Si:25](Cl)([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23].O>CN(C=O)C>[CH:22]([Si:25]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[O:12][CH2:11][C@H:10]1[O:13][C@@H:6]([N:14]2[CH:21]=[CH:20][C:18](=[O:19])[NH:17][C:15]2=[O:16])[CH2:7][C@@H:8]1[OH:9])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 13712DeoxyuridineHCID 139400Triisopropylsilyl chloride

Product 1

HCID 68699325HCID 68699325, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (0.183 g, 2.69 mmol) was added to a solution of 2′-deoxyuridine (0.272 g, 1.19 mmol) in dry DMF (5 mL) under nitrogen. The mixture was cooled in an ice-salt bath before drop-wise addition of triisopropylsilyl chloride (0.28 mL, 1.31 mmol) via a syringe. The reaction mixture was kept at 0° C. for 3 h, allowed to warm up to room temperature and then stirred at room temperature for 22 h. After addition of water (5 mL), the crude mixture was extracted with CHCl3 (2×10 mL). The organic layers were combined and dried over MgSO4. Removal of the solvent under reduced pressure afforded a crude transparent oil which was further purified by flash chromatography eluting the column (ISOLUTE SI) a gradient of 0→10% CH3OH in CHCl3. The title compound was obtained from the fractions with Rf=0.25 (10% CH3OH in CHCl3) as a crystalline white solid (0.366 g, 74%). M.p. 152-153° C.

Workup

  1. extractionthe crude mixture was extracted with CHCl3 (2×10 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent under reduced pressure
  4. customafforded a crude transparent oil which
  5. customwas further purified by flash chromatography
  6. washeluting the column (ISOLUTE SI) a gradient of 0→10% CH3OH in CHCl3

Sources & evidence

ORD record
ord-17d9a5e6208a4ea5b6f748edf7d30598
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

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