Hydrochloric Acid → 3-(3-Methoxy-6-oxopyrido[2,3-b]pyrazin-5(6H)-yl)propanal

HRID 1847016

Reaction equation

[O:1]1CCO[CH:2]1[CH2:6][CH2:7][N:8]1[C:13]2=[N:14][C:15]([O:18][CH3:19])=[CH:16][N:17]=[C:12]2[CH:11]=[CH:10][C:9]1=[O:20].Cl>O1CCCC1>[CH3:19][O:18][C:15]1[N:14]=[C:13]2[N:8]([CH2:7][CH2:6][CH:2]=[O:1])[C:9](=[O:20])[CH:10]=[CH:11][C:12]2=[N:17][CH:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

5-[2-(1,3-Dioxolan-2-yl)ethyl]-3-methoxypyrido[2,3-b]pyrazin-6(5H)-one (397 mg, 1.43 mmol) was dissolved in tetrahydrofuran (15 ml). To the solution was added a 1N hydrochloric acid aqueous solution (5 ml) under cooling on ice and the mixture was stirred at room temperature for two and a half hours and at 50° C. for 4 hours. After cooling in the air, the solvent was removed under reduced pressure and the residue was alkalized by adding saturated sodium bicarbonate water under cooling on ice. The resultant was extracted with dichloromethane, the extract was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 292 mg (87%) of the title compound in the form of a yellowish solid.

Workup

temperatureunder cooling on ice
temperatureAfter cooling in the air
customthe solvent was removed under reduced pressure
additionby adding saturated sodium bicarbonate water
temperatureunder cooling on ice
extractionThe resultant was extracted with dichloromethane
dry with materialthe extract was dried over anhydrous sodium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-34d59c866ecf441c82864c3c65890d83
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952010B2

Linked notes

Loading…