Methyl 5-chloro-6-methylpyrazine-2-carboxylate Chemical Properties

Melting point:

40-43℃

Boiling point:

260℃

Density 

1.314

Flash point:

111℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder

pka

-3.86±0.10(Predicted)

color 

Yellow

InChI

InChI=1S/C7H7ClN2O2/c1-4-6(8)9-3-5(10-4)7(11)12-2/h3H,1-2H3

InChIKey

GGNGFNQPYMKDDR-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC(C)=C(Cl)N=C1

Safety Information

HS Code 

2933199090

Methyl 5-chloro-6-methylpyrazine-2-carboxylate Usage And Synthesis

Pharmaceutical intermediate

The N-methyl-d-aspartate (NMDA) receptor is arguably an important signaling mechanism in the human brain and NMDA receptors play a critical role in regulating the strength of synapses, that is, in regulating synaptic plasticity. Methyl 5-chloro-6-methylpyrazine-2-carboxylate is the key materials to prepare the NMDA receptor.

Uses

Methyl 5-?Chloro-?6-?methylpyrazine-?2-?carboxylate is a reactant used in the synthesis of 4,5-dihydro-5-oxo-2-pyrazinecarboxylic acid 1-oxides.

Synthesis

The general procedure for the synthesis of methyl 5-chloro-6-methylpyrazine-2-carboxylate from methyl 6-methyl-5-oxo-4,5-dihydropyrazine-2-carboxylate was as follows: a solution of methyl 6-methyl-5-oxo-4,5-dihydropyrazine-2-carboxylate was added to POCl3 (20 mL) in DMF (20 mL). The reaction mixture was refluxed for 0.5 h and subsequently poured into ice water. The aqueous layer was extracted with CHCl3 and the organic phase was dried and concentrated with MgSO4. The residue was purified by silica gel column chromatography (eluent: CHCl3) to afford methyl 5-chloro-6-methylpyrazine-2-carboxylate (2.34 g, 52% yield); melting point 49-50 °C.

References

[1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 10, p. 3057 - 3063
[2] Patent: US5811428, 1998, A