Thymidine → 5'-O-(9-Phenylxanthen-9-yl)thymidine

HRID 2393322Notes

Reaction equation

HRID 2393322 reaction equation
Cl[C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[C@@H:22]1([N:30]2[CH:38]=[C:36]([CH3:37])[C:34](=[O:35])[NH:33][C:31]2=[O:32])[O:29][C@H:26]([CH2:27][OH:28])[C@@H:24]([OH:25])[CH2:23]1>N1C=CC=CC=1.C(Cl)Cl>[C:16]1([C:2]2([O:28][CH2:27][C@H:26]3[O:29][C@@H:22]([N:30]4[CH:38]=[C:36]([CH3:37])[C:34](=[O:35])[NH:33][C:31]4=[O:32])[CH2:23][C@@H:24]3[OH:25])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=3[O:9][C:10]3[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 5789ThymidineHCID 1706559-Chloro-9-phenyl-9H-xanthene

Product 1

HCID 109731175'-O-(9-Phenylxanthen-9-yl)thymidineYield 65%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

585 mg (2 mmol) of 9-chloro-9-phenylxanthene were added to a solution of 484 mg (2 mmol) of thymidine in 20 ml of pyridine, and the resulting mixture was stirred at room temperature for 1 hour whilst shading it from light. The reaction mixture was then diluted with 200 ml of methylene chloride, and the diluted mixture was washed twice, each time with 200 ml of a 5% w/v aqueous solution of sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through 35 g of silica gel (70-230 mesh), using methylene chloride containing from 0 to 2.5% by volume of methanol as the eluent, to give 647.8 mg (yield 65%) of the title compound.

Workup

  1. washthe diluted mixture was washed twice
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe residue was purified by column chromatography through 35 g of silica gel (70-230 mesh)

Sources & evidence

ORD record
ord-0b91f42d81314411b4f8ba28849eba81
Source dataset
uspto-grants-1998_09
Patent number
US05807837

Reaction notes

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