Pyridine → 1,3-Dibenzyl-5-(2-thienylacetyl)barbituric acid

HRID 2300041

Reaction equation

[CH2:1]([N:8]1[C:15](=[O:16])[CH2:14][C:12](=[O:13])[N:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][C:36](Cl)=[O:37].CCOCC>ClCCl>[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]([C:36](=[O:37])[CH2:35][C:31]2[S:30][CH:34]=[CH:33][CH:32]=2)[C:12](=[O:13])[N:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1,3-dibenzylbarbituric acid 154 mg (0.500 mmol) in dry dichloromethane 2.0 mL under a nitrogen atmosphere, added was pyridine 1.0 mL (12 mmol) and stirred at 0° C. Added was 2-thienylacetyl chloride 80 mg (0.50 mmol, 1.00 equivalent) in dichloromethane 1.0 mL to the solution slowly during a period of 20 minutes, then stirred at room temperature for 3 hours. Added was ether 50 mL and washed the organic layer with 2 M hydrochloric acid and saturated brine, and dried over sodium sulfate. Purified was the crude product 216 mg after removal of the solvent under the reduced pressure, by column chromatography (silica gel, eluted with dichloromethane). It obtained 1,3-dibenzyl-5-(2-thienylacetyl)barbituric acid 153 mg as yellow viscous oil (56.9% yield).

Workup

additionAdded
customof 20 minutes
stirringstirred at room temperature for 3 hours
additionAdded
washwashed the organic layer with 2 M hydrochloric acid and saturated brine
dry with materialdried over sodium sulfate
customPurified
customafter removal of the solvent under the reduced pressure
washby column chromatography (silica gel, eluted with dichloromethane)

Sources & evidence

ORD record: ord-3c1f3b0149b84b2bb77617a4f1ff0a3c
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498164B1

Linked notes

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