Methyl 5,6-diamino-2-pyridinecarboxylate

Base Information

• Chemical Name: Methyl 5,6-diamino-2-pyridinecarboxylate
• CAS No.: 538372-33-7
• Molecular Formula: C7H9N3O2
• Molecular Weight: 167.17
• Hs Code.: 2933399090
• European Community (EC) Number: 856-249-8
• DSSTox Substance ID: DTXSID20477513
• Wikidata: Q82310268
• Mol file: 538372-33-7.mol

Synonyms:538372-33-7;methyl 5,6-diamino-2-pyridinecarboxylate;methyl 5,6-diaminopyridine-2-carboxylate;METHYL 5,6-DIAMINOPICOLINATE;2-Pyridinecarboxylic acid, 5,6-diamino-, methyl ester;SCHEMBL5554420;DTXSID20477513;YTBZFBYYFHHMHY-UHFFFAOYSA-N;METHYL5,6-DIAMINOPICOLINATE;MFCD10697692;AKOS005073143;AB60256;KD-0703;CS-0371926;FT-0704539;EN300-98497;J-522425;5,6-Diamino-pyridine-2-carboxylic Acid Methyl Ester;5,6-DIAMINO-2-PYRIDINECARBOXYLIC ACID METHYL ESTER

Chemical Property of Methyl 5,6-diamino-2-pyridinecarboxylate

Chemical Property:

• Melting Point: 127～129℃
• Boiling Point: 427.6±40.0 °C(Predicted)
• PKA: 2.41±0.10(Predicted)
• PSA: 91.23000
• Density: 1.336±0.06 g/cm3(Predicted)
• LogP: 1.19500
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 167.069476538
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl 5,6-diamino-2-pyridinecarboxylate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=NC(=C(C=C1)N)N

Technology Process of Methyl 5,6-diamino-2-pyridinecarboxylate

There total 7 articles about Methyl 5,6-diamino-2-pyridinecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

6-amino-5-nitro-pyridine-2-carboxylic acid methyl ester (538372-32-6) → 5,6-diamino-pyridine-2-carboxylic acid methyl ester (538372-33-7)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; at 50 ℃; for 12h;

Reference yield:

6-bromo-3-nitro-pyridin-2-ylamine (84487-04-7) → 5,6-diamino-pyridine-2-carboxylic acid methyl ester (538372-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / Pd(OAc)2; Ph₃P; Et₃N / dimethylformamide / 15 h / 60 °C / 11400 Torr

2: 79 percent / H₂ / Pd/C / methanol; ethyl acetate / 4 h

With palladium diacetate; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja0300158

Reference yield:

6-amino-5-nitro-2-picoline (21901-29-1) → 5,6-diamino-pyridine-2-carboxylic acid methyl ester (538372-33-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 38.5 percent / dimethylformamide / 16 h / 140 °C

2: 1.8 g / potassium carbonate; potassium permanganate / H₂O; 2-methyl-propan-2-ol / 3 h

3: 0.40 g / sulfuric acid / 4 h / Heating

4: 96 percent / H₂ / platinum(IV) oxide / ethanol / 0.5 h / 1551.44 Torr

With potassium permanganate; sulfuric acid; hydrogen; potassium carbonate; platinum(IV) oxide; In ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.bmc.2005.01.042

upstream raw materials:

6-amino-5-nitro-pyridine-2-carboxylic acid methyl ester

6-amino-5-nitropyridine-2-carboxylic acid

6-amino-5-nitro-2-picoline

6-bromo-3-nitro-pyridin-2-ylamine

Downstream raw materials:

2-(4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-yl)-3H-imidazo[4,5-b]pyridine-5-carboxylic acid

2-(4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-yl)-3H-imidazo[4,5-b]pyridine-5-carboxylic acid methyl ester

Refernces

• 1、 Abou-Elkhair, Reham A. I.,Hassan, Abdalla E. A.,Boykin, David W.,Wilson, W. David. "Lithium Hexamethyldisilazane Transformation of Transiently Protected 4-Aza/Benzimidazole Nitriles to Amidines and their Dimethyl Sulfoxide Mediated Imidazole Ring Formation". supporting information. p. 4714 - 4717. Retrieved 2016/09/28.
• 2、 Chand, Pooran,Kotian, Pravin L.,Morris, Philip E.,Bantia, Shanta,Walsh, David A.,Babu, Yarlagadda S.. "Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase". . p. 2665 - 2678. Retrieved 2007/10/03.