Sodium Bicarbonate → 1-(Cyclopent-3-en-1-ylmethyl)-5-ethyl-6-phenylsulfanyl-pyrimidine-2,4-dione

HRID 581849Notes

Reaction equation

HRID 581849 reaction equation
[CH2:1]([C:3]1[C:4](=[O:17])[NH:5][C:6](=[O:16])[NH:7][C:8]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2].C1(C)C(S(O[CH2:28][CH:29]2[CH2:33][CH:32]=[CH:31][CH2:30]2)(=O)=O)=CC=CC=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:29]1([CH2:28][N:7]2[C:8]([S:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[C:3]([CH2:1][CH3:2])[C:4](=[O:17])[NH:5][C:6]2=[O:16])[CH2:33][CH:32]=[CH:31][CH2:30]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 105866375-Ethyl-6-phenylthio-2,4-pyrimidinedioneHCID 86754218HCID 86754218, compound

Product 1

HCID 251596451-(Cyclopent-3-en-1-ylmethyl)-5-ethyl-6-phenylsulfanyl-pyrimidine-2,4-dioneYield 49.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-ethyl-6-phenylthio-2,4-pyrimidinedione (0.10 g, 0.40 mmol) and (cyclopent-3-en-1yl)methyl toluenesulfonate (0.12 g, 0.40 mmol) in dimethylformamide (10 ml ) were heated at 90° C. for overnight in the presence of sodium bicarbonate (41 mg, 0.4 mmol). After the concentration of dimethylformamide under vacuum distillation, the desirable product was obtained as white solid (65 mg) by the separation of column chromatography.

Workup

  1. distillationAfter the concentration of dimethylformamide under vacuum distillation

Sources & evidence

ORD record
ord-7a4cca9848f04446a34acfd216cef1d7
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Reaction notes

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