Thymidine → HCID 22877789, compound

HRID 2393323Notes

Reaction equation

HRID 2393323 reaction equation
Br[C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[C@@H:21]1([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[CH2:22]1>N1C=CC=CC=1>[C:15]1([C:2]2([O:27][CH2:26][C@H:25]3[O:28][C@@H:21]([N:29]4[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]4=[O:31])[CH2:22][C@@H:23]3[OH:24])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:8]3[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 5789ThymidineHCID 2316249-Bromo-9-phenylfluorene

Product 1

HCID 22877789HCID 22877789, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

770 mg (2.4 mmol) of 9-bromo-9-phenylfluorene were added to a solution of 242 mg (1 mmol) of thymidine in 10 ml of pyridine, and the resulting mixture was stirred at 100° C. for 8 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the concentrate was dissolved in 100 ml of methylene chloride. The solution was washed with 100 ml of a 5% w/v aqueous solution of sodium hydrogencarbonate and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 30 g of silica gel (230-400 mesh), using methylene chloride containing from 1 to 3% by volume of methanol as the eluent, to give 194.2 mg (yield 37%) of the title compound.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. dissolutionthe concentrate was dissolved in 100 ml of methylene chloride
  3. washThe solution was washed with 100 ml of a 5% w/v aqueous solution of sodium hydrogencarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through 30 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-497b9faf5fdd4cdb9f2d07dbe19e633e
Source dataset
uspto-grants-1998_09
Patent number
US05807837

Reaction notes

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