8-Amino-3-deazaguanine

Base Information

• Chemical Name: 8-Amino-3-deazaguanine
• CAS No.: 103438-45-5
• Molecular Formula: C₆H₇N₅O
• Molecular Weight: 165.154
• DSSTox Substance ID: DTXSID10145855
• Wikidata: Q83010520
• ChEMBL ID: CHEMBL1179135
• Mol file: 103438-45-5.mol

Synonyms:2,6-diamino-1,5-dihydro-4H-imidazo(4,5-c)pyridin-4-one;8-amino-3-deazaguanine

Chemical Property of 8-Amino-3-deazaguanine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 115.30000
• Density: 1.627g/cm³
• LogP: -0.31190
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 165.06505986
• Heavy Atom Count: 12
• Complexity: 250

Purity/Quality:

99% ^*data from raw suppliers

2,6-diamino-3,5-dihydro-4H-Imidazo[4,5-c]pyridin-4-one 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC(=O)C2=C1NC(=N2)N)N

Technology Process of 8-Amino-3-deazaguanine

There total 5 articles about 8-Amino-3-deazaguanine 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: 18.0%

methyl 2-(benzoylamino)-5-(cyanomethyl)-1H-imidazole-4-carboxylate (103438-49-9) → 2,6-diamino-1,5-dihydro-4H-imidazo<4,5-c>pyridin-4-one (103438-45-5)

Guidance literature:

With ammonia; at 100 ℃; for 144h;

DOI:10.1021/jm00160a040

Reference yield:

3-oxopentanedioic acid dimethyl ester (1830-54-2) → 2,6-diamino-1,5-dihydro-4H-imidazo<4,5-c>pyridin-4-one (103438-45-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 32 percent / p-toluenesulfonic acid / toluene / 24 h / Heating

2: 75 percent / sodium hydride / dimethylformamide / 1 h

3: 74 percent / ammonia / methanol / 72 h / Ambient temperature

4: 57 percent / phosphoryl chloride / 2 h / Heating

5: 18 percent / liquid NH₃ / 144 h / 100 °C

With ammonia; sodium hydride; toluene-4-sulfonic acid; trichlorophosphate; In methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00160a040

Reference yield:

methyl 2-(benzoylamino)-4-(methoxycarbonyl)-1H-imidazole-5-acetate (103438-47-7) → 2,6-diamino-1,5-dihydro-4H-imidazo<4,5-c>pyridin-4-one (103438-45-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / ammonia / methanol / 72 h / Ambient temperature

2: 57 percent / phosphoryl chloride / 2 h / Heating

3: 18 percent / liquid NH₃ / 144 h / 100 °C

With ammonia; trichlorophosphate; In methanol;

DOI:10.1021/jm00160a040

upstream raw materials:

methyl 2-(benzoylamino)-5-(cyanomethyl)-1H-imidazole-4-carboxylate

3-oxopentanedioic acid dimethyl ester

methyl 5-(2-amino-2-oxoethyl)-2-(benzoylamino)-1H-imidazole-4-carboxylate

methyl 2-(benzoylamino)-4-(methoxycarbonyl)-1H-imidazole-5-acetate

Refernces