Uracil → HCID 9870192, compound

HRID 2271255Notes

Reaction equation

HRID 2271255 reaction equation
[C:1]([C@:3]1([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:11][CH:6](OC(=O)C)[C@H:5]([O:12][C:13](=[O:15])[CH3:14])[C@@H:4]1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)#[CH:2].[NH:33]1[CH:40]=[CH:39][C:37](=[O:38])[NH:36][C:34]1=[O:35].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(=O)([O-])O.[Na+]>ClCCCl>[C:1]([C@:3]1([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:11][C@@H:6]([N:33]2[CH:40]=[CH:39][C:37](=[O:38])[NH:36][C:34]2=[O:35])[C@H:5]([O:12][C:13](=[O:15])[CH3:14])[C@@H:4]1[O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)#[CH:2]

Participants

7

Reactant 5

HCID 1174UracilHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 11374009HCID 11374009, compound

Product 1

HCID 9870192HCID 9870192, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Compound 14 (2.5 g, 5.70 mmol) was dissolved in 1,2-dichloroethane (80.0 ml), and uracil (1.60 g, 14.27 mmol) and N,O-bis(trimethylsilyl)acetamide (9.86 ml, 39.74 mmol) were added to the solution, followed by refluxing for one hour. After the reaction mixture was allowed to cool to room temperature, trimethylsilyl trifluoromethanesulfonate (2.06 ml, 11.40 mmol) was added thereto, followed by stirring overnight at 50° C. A saturated aqueous solution of sodium hydrogencarbonate was added to the mixture, and after stirring, precipitate was filtered. The organic layer was dried over anhydrous magnesium sulfate and concentrated through distillation under reduced pressure. The residue was purified by means of silica gel column chromatography (silica gel 300 ml, eluent; n-hexane:ethyl acetate=2:3), to thereby yield a colorless viscous compound (Compound 15; 2.44 g, 4.97 mmol, 87.2%).

Workup

  1. temperatureby refluxing for one hour
  2. stirringafter stirring
  3. filtrationprecipitate was filtered
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated through distillation under reduced pressure
  6. customThe residue was purified by means of silica gel column chromatography (silica gel 300 ml, eluent; n-hexane:ethyl acetate=2:3)

Sources & evidence

ORD record
ord-79390f5e769048b3a0f0a136eef480ce
Source dataset
uspto-grants-2001_12
Patent number
US06333315B1

Reaction notes

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