Thymidine → 5'-O-[(pyren-1-yl)methyl]thymidine

HRID 2393317

반응식

HRID 2393317 반응식
[H-].[Na+].[C@@H:3]1([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[O:10][C@H:7]([CH2:8][OH:9])[C@@H:5]([OH:6])[CH2:4]1.Cl[CH2:21][C:22]1[C:35]2[C:36]3=[C:37]4[C:32](=[CH:33][CH:34]=2)[CH:31]=[CH:30][CH:29]=[C:28]4[CH:27]=[CH:26][C:25]3=[CH:24][CH:23]=1.C(Cl)Cl>CS(C)=O.CO>[C:22]1([CH2:21][O:9][CH2:8][C@H:7]2[O:10][C@@H:3]([N:11]3[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]3=[O:13])[CH2:4][C@@H:5]2[OH:6])[C:35]2[C:36]3=[C:37]4[C:32](=[CH:33][CH:34]=2)[CH:31]=[CH:30][CH:29]=[C:28]4[CH:27]=[CH:26][C:25]3=[CH:24][CH:23]=1

참가 물질

7

반응물 4

HCID 5789ThymidineHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 975811-(Chloromethyl)pyrene

생성물 1

HCID 228777925'-O-[(pyren-1-yl)methyl]thymidine수율 6.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매3회HCID 887Methanol용매

실험 절차

A mixture of 875 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) in 5 ml of dimethyl sulfoxide was stirred at room temperature for 30 minutes in an atmosphere of nitrogen, and then a solution of 2.42 g (10 mmol) of thymidine in 5 ml of dimethyl sulfoxide was added dropwise to the resulting mixture. The mixture was stirred at room temperature for 30 minutes, after which a suspension of 2.51 g (10 mmol) of 1-(chloromethyl)pyrene [Acta Chem. Scand., 10, 1362 (1936)] in 15 ml of dimethyl sulfoxide was added. The mixture was then stirred at room temperature for 90 minutes. At the end of this time, the reaction mixture was poured into 100 ml of ice-water, and the aqueous mixture was extracted with 100 ml of ethyl acetate and then with 100 ml of methylene chloride. The extract was dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through 150 g of silica gel (230-400 mesh), using a gradient elution method, with mixtures of methylene chloride containing from 0 to 4% by volume of methanol as the eluent, to give 292.4 mg (yield 6.4%) of the title compound.

후처리

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. additionwas added
  3. stirringThe mixture was then stirred at room temperature for 90 minutes
  4. extractionthe aqueous mixture was extracted with 100 ml of ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by column chromatography through 150 g of silica gel (230-400 mesh)
  8. washa gradient elution method

출처 및 근거

ORD 기록
ord-e2cc5ea08e39489389e3825f458230e3
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05807837

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