Hydrochloric Acid → 4-[(3R)-3,4-Dihydroxybutyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847070Notes

Reaction equation

CC1(C)[O:6][C@H:5]([CH2:7][CH2:8][N:9]2[C:14](=[O:15])[CH:13]=[N:12][C:11]3[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[N:19][C:10]2=3)[CH2:4][O:3]1.Cl>O1CCCC1>[OH:6][C@@H:5]([CH2:4][OH:3])[CH2:7][CH2:8][N:9]1[C:14](=[O:15])[CH:13]=[N:12][C:11]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[N:19][C:10]1=2

Participants

Conditions

Temperature: 60 °C

Procedure

In tetrahydrofuran (100 ml) was dissolved 4-{2-[(4R)-2,2-dimethyl-1,3-dioxolan-4yl]ethyl}-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (2.55 g, 8.34 mmol), and 1N Hydrochloric acid aqueous solution (25 ml) was added thereto at room temperature and the mixture was stirred at 60° C. for 16 hours. After cooling in the air, the reaction solution was concentrated under reduced pressure and alkalized by adding 1N sodium hydroxide aqueous solution (30 ml) under cooling on ice. The solution was extracted with a lower layer solvent of chloroform/methanol/water (7:3:1) and the extract was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure so as to yield 1.95 g (88%) of the title compound in the form of an orange solid.

Workup

additionwas added
temperatureAfter cooling in the air
concentrationthe reaction solution was concentrated under reduced pressure
additionby adding 1N sodium hydroxide aqueous solution (30 ml)
temperatureunder cooling on ice
extractionThe solution was extracted with a lower layer solvent of chloroform/methanol/water (7:3:1)
dry with materialthe extract was dried over anhydrous sodium sulfate
customThe solvent was removed under reduced pressure so as

Sources & evidence

ORD record: ord-218131c99cd141158ab6e49814a3005f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952010B2

Reaction notes

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