5-Acetylamino-6-amino-3-methyluracil

Base Information

• Chemical Name: 5-Acetylamino-6-amino-3-methyluracil
• CAS No.: 19893-78-8
• Molecular Formula: C₇H₁₀N₄O₃
• Molecular Weight: 198.181
• Hs Code.: 2933599090
• UNII: R1KU8R8Z0C
• DSSTox Substance ID: DTXSID20173669
• Nikkaji Number: J128.135F
• Wikidata: Q27149524
• Metabolomics Workbench ID: 38523
• ChEMBL ID: CHEMBL1899490
• Mol file: 19893-78-8.mol

Synonyms:5-acetylamino-6-amino-3-methyluracil;5-AMMU

Chemical Property of 5-Acetylamino-6-amino-3-methyluracil

Chemical Property:

• Melting Point: ≥305 °C
• PSA: 109.98000
• Density: 1.45g/cm³
• LogP: -0.73160
• Storage Temp.: 2-8°C
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 198.07529019
• Heavy Atom Count: 14
• Complexity: 347

Purity/Quality:

97% ^*data from raw suppliers

N-(6-Amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=C(NC(=O)N(C1=O)C)N

Technology Process of 5-Acetylamino-6-amino-3-methyluracil

There total 5 articles about 5-Acetylamino-6-amino-3-methyluracil 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: 97.0%

5,6-diamino-3-methylpyrimidine-2,4(1H,3H)-dione (40959-24-8) + acetic anhydride (108-24-7) → 5-Acetylamino-6-amino-3-methyluracil (19893-78-8)

Guidance literature:

With sodium acetate; acetic acid; for 3h; Heating;

DOI:10.1515/znb-1997-1214

Reference yield:

3-methyl-6-aminouracil (21236-97-5) → 5-Acetylamino-6-amino-3-methyluracil (19893-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / aq. NaOAc, AcOH, NaNO₂ / 0.5 h / 100 °C

2: 82 percent / H₂, NaOH / 10percent Pd/C / methanol; H₂O / 20 °C / 2625.2 Torr

3: 97 percent / NaOAc, glacial AcOH / 3 h / Heating

With sodium hydroxide; hydrogen; sodium acetate; acetic acid; sodium nitrite; palladium on activated charcoal; In methanol; water;

DOI:10.1515/znb-1997-1214

Reference yield:

6-amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (54030-56-7) → 5-Acetylamino-6-amino-3-methyluracil (19893-78-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / 1N aq. NaOH / 2 h / Heating

2: 95 percent / aq. NaOAc, AcOH, NaNO₂ / 0.5 h / 100 °C

3: 82 percent / H₂, NaOH / 10percent Pd/C / methanol; H₂O / 20 °C / 2625.2 Torr

4: 97 percent / NaOAc, glacial AcOH / 3 h / Heating

With sodium hydroxide; hydrogen; sodium acetate; acetic acid; sodium nitrite; palladium on activated charcoal; In methanol; water;

DOI:10.1515/znb-1997-1214

upstream raw materials:

5,6-diamino-3-methylpyrimidine-2,4(1H,3H)-dione

acetic anhydride

3-methyl-6-aminouracil

6-amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one

Downstream raw materials:

5-Acetylamino-6-formylamino-3-methyluracil

Refernces

• 1、 Roehrkasten,Raatz,Kreher,Blaszkewicz. "Synthesis of the caffeine metabolites 5-acetylamino-6-formylamino-3-methyluracil (AFMU) and 5-acetylamino-6-amino-3-methyluracil (AAMU) on a preparative scale". . p. 1526 - 1532. Retrieved 2007/10/03.