Lithium iodide → 1-[2-(Cyclopent-1-en-1-yl)ethyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione

HRID 581880

Reaction equation

C(=O)(O)[O-].[Na+].[I-].[Li+].[CH2:8]([C:10]1[C:11](=[O:27])[NH:12][C:13](=[O:26])[NH:14][C:15]=1[C:16](=[O:25])[C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)[CH3:9].C1(C)C(S(O[CH2:38][CH2:39][C:40]2[CH2:44][CH2:43][CH2:42][CH:41]=2)(=O)=O)=CC=CC=1>CN(C)C=O>[C:40]1([CH2:39][CH2:38][N:14]2[C:15]([C:16](=[O:25])[C:17]3[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=3)=[C:10]([CH2:8][CH3:9])[C:11](=[O:27])[NH:12][C:13]2=[O:26])[CH2:44][CH2:43][CH2:42][CH:41]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of sodium bicarbonate (0.10 g, 1.2 mmol) and lithium iodide (13 mg, 0.1 mmol) were added to dimethylformamide solution (10 ml) of 5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione (0.27 g, 1.0 mmol) and 2-(cyclopent-1-en-1-yl)ethyl toluenesulfonate (0.27 g, 1.0 mmol). And then, the reaction mixture was stirred at 90° C. for overnight, concentrated for removement of dimethylformamide, extracted with dichloromethane, dried, filtered and separated by column chromatography to give a desirable product as a white solid (148 mg).

Workup

concentrationconcentrated for removement of dimethylformamide
extractionextracted with dichloromethane
customdried
filtrationfiltered
customseparated by column chromatography

Sources & evidence

ORD record: ord-08fb5b5271d448cf9530bbfd9ee00e0c
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922727

Linked notes

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