Pyridine → 1,3-Bis(3-methylbutyl)-5-(3-methyl-1-oxobutyl)barbituric acid

HRID 2300042Notes

Reaction equation

[CH3:1][CH:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:12](=[O:13])[CH2:11][C:9](=[O:10])[N:8]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:6]1=[O:7].N1C=CC=CC=1.[C:26](Cl)(=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29]>ClCCl>[CH3:17][CH:16]([CH3:18])[CH2:15][CH2:14][N:8]1[C:9](=[O:10])[CH:11]([C:26](=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29])[C:12](=[O:13])[N:5]([CH2:4][CH2:3][CH:2]([CH3:19])[CH3:1])[C:6]1=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1,3-bis(3-methylbutyl)barbituric acid 268 mg (1.00 mmol) in dry dichloromethane 3.0 mL under a nitrogen atmosphere, added was pyridine 0.81 mL (0.79 g, 10 mmol, 10 equivalents) and stirred at 0° C. Added was isovaleryl chloride 121 mg (1.00 mmol, 1.00 equivalent) in dichloromethane 1.5 mL to the solution slowly during a period of 20 minutes, then stirred at room temperature for 4 hours. Added was dichloromethane 40 mL and washed the organic layer with 2 M hydrochloric acid and saturated brine, and dried over sodium sulfate. Purified was the crude product 383 mg, after removal of the solvent under the reduced pressure, by column chromatography (silica gel, eluted with dichloromethane). It obtained 1,3-bis(3-methylbutyl)-5-(3-methyl-1-oxobutyl)barbituric acid 278 mg as white plates (79.0% yield).

Workup

additionAdded
customof 20 minutes
stirringstirred at room temperature for 4 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-ae657e249fab442d811d13102449de0b
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498164B1

Reaction notes

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