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Imidazole → 1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione

HRID 1907099
Notes
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Reaction equation

HRID 1907099 reaction equation
[I:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C)C=O>[Si:27]([O:13][CH2:12][C@H:11]1[O:14][C@@H:7]([N:6]2[CH:15]=[C:2]([I:1])[C:3](=[O:17])[NH:4][C:5]2=[O:16])[CH2:8][C@@H:9]1[OH:10])([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5905IdoxuridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 100276201-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

To a solution of 5-iodo-2′-deoxyuridine (5.0 g, 14 mmol) in 70 ml in dry N,N-dimethylformamide (DMF) was added imidazole (1.09 g, 16 mmol), followed by (2.41 g, 16 mmol) TBDMSCl at 0° C. The mixture was left in the ice bath and stirred overnight. The reaction was quenched with sat. aq. NaCl solution and extracted with EtOAc. After drying (MgSO4), the solvent was removed and the crude mixture was purified by chromatography on silica (EtOAc:petroleum ether 3:7). The product (33) (5.9 g, 90%) was obtained as a colourless solid. 1H NMR (d6 DMSO) δ 0.00 (s, 3H, CH3), 0.79 (s, 9H, tBu), 1.88-1.97 (m, 1H, H-2′), 2.00-2.05 (m, 1H, H-2′), 3.59-3.71 (m, 2H, H-5′), 3.75 (br s, 1H, H-4′), 4.06 (br s, 1H, H-3′), 5.18 (d, J=4.0 Hz, 1H, OH), 5.98 (t, J=5.9 Hz, 1H, H-1′), 7.89 (s, 1H, H-6), 11.62 (s, 1H, NH). Mass (−ve electrospray) calcd for C15H25IN2O5Si 468.06. Found 467.

Workup

  1. customThe reaction was quenched with sat. aq. NaCl solution
  2. extractionextracted with EtOAc
  3. dry with materialAfter drying (MgSO4)
  4. customthe solvent was removed
  5. customthe crude mixture was purified by chromatography on silica (EtOAc:petroleum ether 3:7)

Sources & evidence

ORD record
ord-c190ff36700d434fa2969d20f9651141
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08597881B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes