Imidazole → HCID 24767999, compound

HRID 556258Notes

Reaction equation

HRID 556258 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:9]([C@@:11]1([OH:27])[C@@H:15]([CH2:16][OH:17])[O:14][C@@H:13]([N:18]2[CH:25]=[CH:24][C:22]([NH2:23])=[N:21][C:19]2=[O:20])[C@@H:12]1[OH:26])#[CH:10].N1C=CN=C1>CN(C)C=O>[Si:1]([O:17][CH2:16][C@H:15]1[O:14][C@@H:13]([N:18]2[CH:25]=[CH:24][C:22]([NH2:23])=[N:21][C:19]2=[O:20])[C@H:12]([OH:26])[C@:11]1([C:9]#[CH:10])[OH:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1768851-(3-C-Ethynylpentofuranosyl)-4-imino-1,4-dihydropyrimidin-2-ol2×

Product 1

HCID 24767999HCID 24767999, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

tert-Butyldimethylsilylchloride (12.5 g, 82.5 mmol) was gradually added under ice-cooling to a solution of 3′-ethynylcytidine (hereinafter referred to as ECyd) (20 g, 75 mmol) and imidazole (12.8 g, 188 mmol) in N,N-dimethylformamide (hereinafter referred to as DMF) (75 mL), and the mixture was stirred for 5 hours at room temperature. After completion of reaction, the solvent was evaporated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with saturated aqueous sodium hydrogen carbonate (100 mL) and saturated brine (100 mL) and dried with magnesium sulfate. Magnesium sulfate was removed through filtration. The filtrate was stirred at room temperature, and precipitated crystals were collected through filtration, to thereby yield Compound 1 (11.5 g, 52%).

Workup

  1. customAfter completion of reaction
  2. customthe solvent was evaporated under reduced pressure, and ethyl acetate
  3. additionwas added to the residue
  4. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate (100 mL) and saturated brine (100 mL)
  5. dry with materialdried with magnesium sulfate
  6. customMagnesium sulfate was removed through filtration
  7. stirringThe filtrate was stirred at room temperature
  8. customprecipitated crystals
  9. filtrationwere collected through filtration

Sources & evidence

ORD record
ord-56c3e20e928d48aab4cdea1f1508c78c
Source dataset
uspto-grants-2011_11
Patent number
US08058261B2

Reaction notes

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