Methyl 5-chloropyrazine-2-carboxylate
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Methyl 5-chloropyrazine-2-carboxylate
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CAS No:
33332-25-1
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Formula:
C6H5ClN2O2
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Chemical Name:
Methyl 5-chloropyrazine-2-carboxylate
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Synonyms:
methyl 5-chloropiperazine-2-carboxylate;Methyl 5-chloropyrazine-2...;2-Chloro-5-(methoxycarbonyl)pyrazine;2-chloro-5-carboMethoxy-pyrazine;2-Chloro-5-(methoxycarbonyl)pyrazine, 2-Chloro-5-(methoxycarbonyl)-1,4-diazine;5 - Methyl chloride pyrazine - 2 - carboxylic acid;Methyl 5-chloro-2-pyrazinecarboxylate >=98.0% (HPLC);5-CHLORO-PYRAZINE-2-CARBOXYLIC ACID METHYL ESTER
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CAS No:
Characteristics
52.1
0.5
Solid
1.4±0.1 g/cm3
89-90 °C(Solv: ligroine (8032-32-4))
242.8°C at 760 mmHg
100.6±25.9 °C
1.534
Safety Information
IRRITANT
NONH for all modes of transport
3
36/37/38
26
Xi
P261-P305 + P351 + P338
H315-H319-H335
Methyl 5-chloropyrazine-2-carboxylate Use and Manufacturing
(62b) Preparation 415-Chloro-pyrazine-2-carboxylic acid methyl esterA mixture of 5-hydroxy-pyrazine-2-carboxylic acid methyl ester (Preparation 40, 50 g, 324mmol) and POCITo a solution of 5-chloropyrazine-2-carboxylic acid (300 mg, 1.89 mmol) in CH2C12 (3.8 mL) was added EDCI (401 mg, 2.09 mmol), DMAP (12.5 mg, 0.102 mmol) and MeOH (0.15 mL, 3.7 mmol) at room temperature. After stirring for 2 h, the reaction was quenched by adding saturated NH4C1 solution. The crude products were extracted with CH2C12 (x3), and the combined organic extracts were washed with brine, dried (MgS04), and concentrated in vacuo. The residue was purified by flash column chromatography (hexane/EtOAc = 9/1 to 7/1) to afford methyl 5-chloropyrazine-2-carboxylate (213 g, 65percent) as a white solid. NMR (300 MHz, CDCh) δ 9.12 (d, J = 1.8 Hz, 1H), 8.73 (d, J = 1.8 Hz, 1H), 4.07 (s, 3H).(5-chloropyrazin-2-yl)methyl methanesulfonate; [00369] To a solution of 5-chloropyrazine-2-carboxylic acid (3.21 g, 20.3 mmol) in diethyl ether (20 mL) and methanol (20.0 mL) was added a 2M solution in diethyl ether of trimethylsilyldiazomethane (20.3 mL, 40.5 mmol). A vigorous bubbling was observed initially, and LCMS after 30 minutes indicated that the reaction was complete.Concentration of the reaction mixture afforded methyl 5-chloropyrazine-2-carboxylate (3.53 g, 20.5 mmol, 101percent yield) as a tan solid. This material was shown to be >95percent pure by NMR analysis and was used in the subsequent step without any purification.
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Methyl 5-chloropyrazine-2-carboxylate
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