3-AMINO-6-IODOPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER Chemical Properties

Melting point:

200-202℃

Boiling point:

387.9±42.0 °C(Predicted)

Density 

2.020±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

2-8°C, protect from light

form 

Solid

pka

-1.59±0.10(Predicted)

Appearance

Yellow to brown Solid

Sensitive 

Light Sensitive

InChI

InChI=1S/C6H6IN3O2/c1-12-6(11)4-5(8)9-2-3(7)10-4/h2H,1H3,(H2,8,9)

InChIKey

FDLARAKNPMCCKJ-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC(I)=CN=C1N

3-AMINO-6-IODOPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Uses

Methyl 3-amino-6-iodopyrazine-2-carboxylate

Synthesis

General procedure for the synthesis of methyl 3-amino-6-iodopyrazine-2-carboxylate from methyl 3-aminopyrazine-2-carboxylate: 1.5 equivalents of N-iodosuccinimide (NIS) was added to a 25 mL solution of dimethylformamide (DMF) containing 5 g (32.7 mmol) of methyl 3-aminopyrazine-2-carboxylate at room temperature. The reaction mixture was heated to 65 °C and after 1 hour of reaction, 0.5 equivalents of N-iodosuccinimide (NIS) was added and the reaction was continued at 65 °C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and the solvent was removed by rotary evaporation. Subsequently, the product was extracted several times with dichloromethane. The organic phases were combined, washed with 10% sodium bisulfite solution, dried over anhydrous magnesium sulfate, and concentrated to give 8 g (88% yield) of the yellow solid product methyl 3-amino-6-iodopyrazine-2-carboxylate. The product was analyzed by LC-MS (EI) at m/z (M+1) of 280. 1H NMR (400 MHz, DMSO-d6) δ: 8.50 (1H, s, Ar-H), 7.50 (2H, br s, NH2), 3.20 (3H, s, OCH3).

References

[1] Chemistry - A European Journal, 2017, vol. 23, # 47, p. 11230 - 11233
[2] Patent: WO2012/101239, 2012, A1. Location in patent: Page/Page column 56
[3] Patent: US2013/85144, 2013, A1. Location in patent: Paragraph 0288; 0289; 0290
[4] Patent: EP2689778, 2014, A1. Location in patent: Paragraph 0188
[5] Patent: WO2014/16433, 2014, A1. Location in patent: Page/Page column 55

3-AMINO-6-IODOPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER(1458-16-8)Related Product Information

• Methyl 3-amino-6-chloropyrazine-2-carboxylate
• 3-AMINO-4-METHOXYPYRIDINE
• 3-AMINO-3-(4-CYANOPHENYL)PROPANOIC ACID
• 3-Amino-5-chloropyridin-2-ol HCl
• (3-aminopyrazin-2-yl)methanol
• 3-Amino-3-(4-methoxyphenyl)propionic acid
• 3-PYRIDINAMINE, 6-(1-METHYLETHYL)-
• 3-AMINO-5-HYDROXYBENZOIC ACID
• 2-CHLORO-5-IODO-PYRIDIN-3-YLAMINE
• 2-CHLORO-5-(TRIFLUOROMETHYL)-3-PYRIDINAMINE
• Methyl triazole-3-carboxylate
• Iodopyrazine
• METHYL PYRAZINE-2-CARBOXYLATE
• 3-AMINO-6-IODOPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER
• 2-AMINO-5-IODOPYRAZINE
• 3-AMINO-6-IODOPYRAZINE-2-CARBOXYLIC ACID
• 2-AMINO-5-IODO-3-METHYLPYRAZINE
• 2-IODOPYRAZINE