5-(1,3-Benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one

Base Information

• Chemical Name: 5-(1,3-Benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one
• CAS No.: 72716-71-3
• Molecular Formula: C12H10 N4 O5
• Molecular Weight: 290.235
• Hs Code.: 2934999090
• European Community (EC) Number: 276-779-8
• DSSTox Substance ID: DTXSID40223019
• Mol file: 72716-71-3.mol

Synonyms:72716-71-3;5-(1,3-Benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one;N-[5-(1,3-benzodioxol-5-ylmethyl)-6-oxo-1H-pyrimidin-2-yl]nitramide;N-(5-(Benzo[d][1,3]dioxol-5-ylmethyl)-6-oxo-1,6-dihydropyrimidin-2-yl)nitramide;EINECS 276-779-8;DTXSID40223019;CYDVFWXIUURXJS-UHFFFAOYSA-N;NS00037397

Chemical Property of 5-(1,3-Benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one

Chemical Property:

• Vapor Pressure: 4.56E-10mmHg at 25°C
• Refractive Index: 1.74
• Boiling Point: 498.4°C at 760 mmHg
• Flash Point: 255.2°C
• PSA: 122.32000
• Density: 1.7g/cm³
• LogP: 1.70150
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 290.06511943
• Heavy Atom Count: 21
• Complexity: 512

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)CC3=CN=C(NC3=O)N[N+](=O)[O-]

Technology Process of 5-(1,3-Benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one

There total 4 articles about 5-(1,3-Benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one 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:

piperonal (120-57-0,30024-74-9) → 5-(1,3-benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one (72716-71-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) piperidine, 2) conc. H₂SO₄ / 1) pyridine

2: hydrogen / 5percent Pd/C / ethanol

3: sodium wire / diethyl ether / 18 h / Ambient temperature

4: 1) NaOMe / 1) MeOH, reflux, 45 min, 2) MeOH, reflux, 18 h

With piperidine; sulfuric acid; hydrogen; sodium methylate; sodium; palladium on activated charcoal; In diethyl ether; ethanol;

DOI:10.1016/0223-5234(88)90167-5

Reference yield:

ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate (24393-66-6) → 5-(1,3-benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one (72716-71-3)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen / 5percent Pd/C / ethanol

2: sodium wire / diethyl ether / 18 h / Ambient temperature

3: 1) NaOMe / 1) MeOH, reflux, 45 min, 2) MeOH, reflux, 18 h

With hydrogen; sodium methylate; sodium; palladium on activated charcoal; In diethyl ether; ethanol;

DOI:10.1016/0223-5234(88)90167-5

Reference yield:

3-benzo[1,3]dioxol-5-yl-propionic acid ethyl ester (7116-48-5) → 5-(1,3-benzodioxol-5-ylmethyl)-2-(nitroamino)-1H-pyrimidin-4-one (72716-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium wire / diethyl ether / 18 h / Ambient temperature

2: 1) NaOMe / 1) MeOH, reflux, 45 min, 2) MeOH, reflux, 18 h

With sodium methylate; sodium; In diethyl ether;

DOI:10.1016/0223-5234(88)90167-5

upstream raw materials:

nitroguanidine

piperonal

3-benzo[1,3]dioxol-5-yl-propionic acid ethyl ester

ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate

Downstream raw materials:

Oxmetidine hydrochloride

2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(3-methoxybenzyl)-4-pyrimidone dihydrochloride

Refernces