Methyl 3-amino-2-pyrazinecarboxylate Chemical Properties

Melting point:

169-172 °C (lit.)

Boiling point:

300.8±37.0 °C(Predicted)

Density 

1.319±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform, Methanol

pka

-0.30±0.10(Predicted)

form 

Crystalline Powder

color 

Yellow

BRN 

127495

InChIKey

INCSQLZZXBPATR-UHFFFAOYSA-N

LogP

0.2 at 20℃ and pH7

Surface tension

73.3mN/m at 1g/L and 20℃

CAS DataBase Reference

16298-03-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Methyl 3-amino-2-pyrazinecarboxylate Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

Methyl 3-amino-2-pyrazinecarboxylate has been used in:

• synthesis of 2-arylpteridin-4-ones and piperazine-derived 2-furan-2-yl-[1,2,4]triazolo[1,5-a] pyrazines
• reactions with isocyanates and aroyl chlorides for conversion to pteridinediones

Definition

ChEBI: Methyl 3-aminopyrazine-2-carboxylate is a pyrazine that is substituted by a methoxycarbonyl group at position 2 and an amino group at position 3. It is a member of pyrazines, a methyl ester and an aromatic amine.

Synthesis

General procedure for the synthesis of methyl 3-aminopyrazine-2-carboxylate from methanol and 3-aminopyrazine-2-carboxylic acid: 3-aminopyrazine-2-carboxylic acid (5 g, 1 eq.) was added to methanol (50 ml) followed by the slow addition of concentrated sulphuric acid (4 eq.) under ice-water bath conditions. The reaction mixture was stirred at room temperature and the progress of the reaction was monitored by thin layer chromatography (TLC) until completion of the reaction. Upon completion of the reaction, the reaction solution was concentrated and the pH was adjusted with saturated sodium carbonate solution to 8. The precipitate was collected by filtration and dried at 50 °C for 2 h to afford methyl 3-aminopyrazine-2-carboxylate as a brown solid (4.18 g, 76% yield).

Purification Methods

The ester forms yellow needles from H2O (100 parts using charcoal). If it contains the free acid (see IR), then dissolve it in CH2Cl2, wash it with saturated aqueous Na2CO3, brine, dry over MgSO4 filter, evaporate and recrystallise the residue. The free acid has m 203-204o (dec) [UV: Brown & Mason J Chem Soc 3443 1956] and pK1 <1 and pK2 3.70. The ammonium salt has m 232o(dec) (from aqueous Me2CO) and the amide has m 239.2o (from H2O) [Ellingson et al. J Am Chem Soc 67 1711 1945]. [Beilstein 25 III/IV 4412.]

References

[1] Journal of Molecular Structure, 2005, vol. 741, # 1-3, p. 67 - 75
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2784 - 2788
[3] Patent: CN106866553, 2017, A. Location in patent: Paragraph 0137; 0138; 0139; 0140
[4] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 4, p. 865 - 872
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10475 - 10489

Methyl 3-amino-2-pyrazinecarboxylate(16298-03-6)Related Product Information

• METSULFURON METHYL
• Bensulfuron methyl
• Phenyl carbamate
• Methyl 2-[2-chloro-4-fluoro-5-[(3-oxo-5,6,7,8-tetrahydro-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]sulfanylacetate
• 2-Pyrazinecarboxylic acid
• 3-Aminopyrazine-2-carboxylic acid
• Aminopyrazine
• Methyl 5-chloropyrazine-2-carboxylate
• Methyl acetate
• Glipizide
• Methyl anthranilate
• Kresoxim-methyl
• Methylparaben
• Methyl salicylate
• Methyl carbamate
• Pyrazinamide
• Thiophanate-methyl
• Methyl 3-amino-2-thiophenecarboxylate