ChemicalBook--->CAS DataBase List--->13924-95-3

13924-95-3

13924-95-3 Structure

13924-95-3 Structure
IdentificationBack Directory
[Name]

5-Hydroxypyrazine-2-carboxylic acid methyl ester
[CAS]

13924-95-3
[Synonyms]

CBI-BB ZERO/008486
Methyl 5-hydropyrazine-2-carboxylate
METHYL 5-HYDROXYPYRAZINE-2-CARBOXYLATE
methyl-5-hydroxy-2-pyrazinecarboxylate
methyl 6-oxo-1H-pyrazine-3-carboxylate
Methyl 5-hydroxypyrazine-2-carboxylate 95%
methyl 5-oxo-4,5-dihydropyrazine-2-carboxylate
Methyl 5-oxo-4,5-dihydro-2-pyrazinecarboxylate
5-Hydrocy-pyrazine-2-carboxylic acid methyl ester
5-HYDROXY-PYRAZINE-2-CARBOXYLIC ACID METHYL ESTER
5-HYDROXY-PYRAZINE-2-CARBOXYLIC ACID METHYL ESTER 95%
Pyrazinecarboxylic acid, 4,5-dihydro-5-oxo-, methyl ester
2-Pyrazinecarboxylic acid, 4,5-dihydro-5-oxo-, methyl ester
5-Hydroxypyrazine-2-carboxylic acid methyl ester ISO 9001:2015 REACH
2-Hydroxy-5-(methoxycarbonyl)pyrazine, 2-Hydroxy-5-(methoxycarbonyl)-1,4-diazine
[EINECS(EC#)]

1312995-182-4
[Molecular Formula]

C6H6N2O3
[MDL Number]

MFCD08273469
[MOL File]

13924-95-3.mol
[Molecular Weight]

154.12
Chemical PropertiesBack Directory
[Melting point ]

183-185 °C
[density ]

1.39
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

10.55±0.40(Predicted)
[Appearance]

White to light brown Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H319-H335-H302+H312+H332-H315
[Precautionary statements ]

P280
[HS Code ]

2933998090
Hazard InformationBack Directory
[Uses]

5-Hydroxypyrazine-2-carboxylic Acid Methyl Ester is a metabolite of Pyrazinamide (P840600), an antibacterial (tuberculostatic).
[Synthesis]

Methanol

67-56-1

5-Hydroxypyrazine-2-carboxylic acid

34604-60-9

5-Hydroxypyrazine-2-carboxylic acid methyl ester

13924-95-3

General procedure for the synthesis of methyl 5-hydroxypyrazine-2-carboxylate from methanol and 5-oxo-4,5-dihydropyrazine-2-carboxylic acid: Acetyl chloride (152 mL, 2.08 mol) was slowly added dropwise to methanol (5 L) at -20 °C. After the dropwise addition was completed, stirring was continued at this temperature for 30 minutes. Subsequently, 5-hydroxypyrazine-2-carboxylic acid (100 g, 714 mmol) was added and the mixture was heated to reflux and the reaction was maintained for 2 hours. Upon completion of the reaction, the solvent was removed by vacuum concentration and the residue was recrystallized from methanol (400 mL) to give 71 g (464 mmol) of methyl 5-hydroxypyrazine-2-carboxylate in 65% yield.

[References]

[1] Patent: WO2013/14567, 2013, A1. Location in patent: Page/Page column 80-81
[2] Patent: EP2239253, 2010, A1. Location in patent: Page/Page column 96
[3] Patent: EP1452525, 2004, A1. Location in patent: Page 15
Spectrum DetailBack Directory
[Spectrum Detail]

5-Hydroxypyrazine-2-carboxylic acid methyl ester(13924-95-3)1HNMR
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34604-60-9 6164-79-0 77168-84-4