Hydrochloric Acid → HCID 59571074, compound

HRID 2192929Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][O:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:19]1[N:20]=[CH:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[N:23][CH:24]=1.Cl>CN1CCCC1=O>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][O:8][C:9]([CH3:13])([CH3:12])[CH2:10][O:11][C:19]2[N:20]=[CH:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[N:23][CH:24]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-[(4-methoxybenzyl)oxy]-2-methylpropan-1-ol (0.30 g) in N-methylpyrrolidone (4.5 mL) was added sodium hydride (63 mg) under ice-cooling, followed by stirring at 60° C. for 30 minutes. To the reaction mixture was added methyl 5-chloropyrazine-2-carboxylate (246 mg), followed by stirring at 120° C. overnight. To the reaction mixture was added 1 M hydrochloric acid for neutralization in an ice bath, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20) to obtain methyl 5-{2-[(4-methoxybenzyl)oxy]-2-methylpropoxy}pyrazine-2-carboxylate (0.20 g) as a colorless oily substance.

Workup

temperaturecooling
stirringby stirring at 120° C. overnight
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20)

Sources & evidence

ORD record: ord-aadb7a2bd79248b689bbc37b1509be25
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329707B2

Reaction notes

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