Potassium Carbonate → HCID 86751372, compound

HRID 1488556Notes

Reaction equation

HRID 1488556 reaction equation
[SH:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17].Cl[CH2:19][C:20]1[C:21]2[C:26]([CH:27]=[C:28]3[C:33]=1[CH:32]=[CH:31][CH:30]=[CH:29]3)=[CH:25][CH:24]=[CH:23][CH:22]=2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:22]1[C:21]2[C:26](=[CH:27][C:28]3[C:33]([C:20]=2[CH2:19][S:1][CH2:2][C@H:3]2[O:7][C@@H:6]([N:8]4[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]4=[O:10])[CH2:5][C@@H:4]2[OH:17])=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 323859-(Chloromethyl)anthraceneHCID 15277004HCID 15277004, compound

Product 1

HCID 86751372HCID 86751372, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

258 mg (1 mmol) of 5'-deoxy-5'-mercaptothymidine was added to 20 ml of acetone. 272 mg (1.2 mmol) of 9-chloromethylanthracene and 1 g of anhydrous potassium carbonate were then added to the solution under an atmosphere of nitrogen. The resulting mixture was then stirred whilst being heated under reflux for 2 hours. At the end of this time, precipitates were filtered off from the reaction mixture, and the filtrate was freed from the solvent by distillation under reduced pressure. The residue was crystallized from 10 ml of ethanol, to give 156 mg (yield 35%) of the title compound as pale yellow crystals.

Workup

  1. temperaturewhilst being heated
  2. temperatureunder reflux for 2 hours
  3. customAt the end of this time, precipitates
  4. filtrationwere filtered off from the reaction mixture
  5. distillationthe filtrate was freed from the solvent by distillation under reduced pressure
  6. customThe residue was crystallized from 10 ml of ethanol

Sources & evidence

ORD record
ord-5d6c3d1b0e814f6783c9ea684ca72e42
Source dataset
uspto-grants-1997_10
Patent number
US05674856

Reaction notes

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