Sodium Bicarbonate → 1-[(Cyclopent-1-en-1-yl)methyl]-5-ethyl-6-phenylthio-2,4-pyrimidinedione

HRID 581852Notes

Reaction equation

HRID 581852 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>[C: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][CH2:32][CH2:31][CH:30]=1

Participants

5

Reactant 3

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

Product 1

HCID 540561251-[(Cyclopent-1-en-1-yl)methyl]-5-ethyl-6-phenylthio-2,4-pyrimidinedioneYield 34.3%

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, 0.48 mmol). After the concentration of dimethylformamide under vacuum distillation, the desirable product was obtained as white solid (45 mg) by the separation of column chromatography.

Workup

  1. distillationAfter the concentration of dimethylformamide under vacuum distillation

Sources & evidence

ORD record
ord-30e85e26f0ba4a55b97d0b45c4a30a97
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Reaction notes

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