6-Amino-1-benzyluracil

Base Information

• Chemical Name: 6-Amino-1-benzyluracil
• CAS No.: 41862-11-7
• Molecular Formula: C11H11N3O2
• Molecular Weight: 217.227
• Hs Code.: 2933599090
• NSC Number: 70496
• DSSTox Substance ID: DTXSID50290717
• Nikkaji Number: J1.245.700F
• Wikidata: Q82028494
• ChEMBL ID: CHEMBL1489220
• Mol file: 41862-11-7.mol

Synonyms:6-Amino-1-benzyluracil;41862-11-7;6-amino-1-benzylpyrimidine-2,4(1H,3H)-dione;6-amino-1-benzylpyrimidine-2,4-dione;1-benzyl-6-aminouracil;CC-PMLSC- DMA-P111;MFCD00205031;NSC 70496;6-amino-1-benzyl-1,2,3,4-tetrahydropyrimidine-2,4-dione;6-amino-1-benzyl-2,4(1H,3H)-pyrimidinedione;NSC70496;6-amino-1-benzyl-1,3-dihydropyrimidine-2,4-dione;N-Acetoacetylcresidine;6-amino-1-benzyl Uracil;ChemDiv3_003424;Oprea1_320204;MLS000889040;cid_250746;SCHEMBL1032784;SCHEMBL4015393;CHEMBL1489220;BDBM35449;1-BENZYL-6-AMINO-URACIL;DTXSID50290717;HMS1482L14;HMS2195F18;HMS3348O13;CCG-5022;BBL012881;NSC-70496;STK645666;STK788839;AKOS000115166;AKOS005576846;CCG-112356;SB58200;SDCCGMLS-0091912.P001;NCGC00142308-01;6-amino-1-benzyl-pyrimidine-2,4-quinone;SMR000209018;VS-03564;CS-0307498;EU-0012095;FT-0661610;EN300-01363;6-amino-1-(phenylmethyl)pyrimidine-2,4-dione;6-azanyl-1-(phenylmethyl)pyrimidine-2,4-dione;F83596;6-amino-1-benzyl-4-hydroxypyrimidin-2(1H)-one;AB-323/25048020;W-202720;BRD-K75882205-001-01-7;Z56824668;F1168-0001

Chemical Property of 6-Amino-1-benzyluracil

Chemical Property:

• Appearance/Colour: off-white solid
• Melting Point: 289-291 °C (dec.)
• Refractive Index: 1.625
• PSA: 80.88000
• Density: 1.326 g/cm³
• LogP: 0.74830
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 217.085126602
• Heavy Atom Count: 16
• Complexity: 332

Purity/Quality:

99% ^*data from raw suppliers

6-Amino-1-benzyluracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C(=CC(=O)NC2=O)N

Technology Process of 6-Amino-1-benzyluracil

There total 7 articles about 6-Amino-1-benzyluracil 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: 93.0%

1-benzyl-3-(2-cyanoacetyl)urea (126245-46-3) → 1-benzyl-6-aminouracil (41862-11-7)

Guidance literature:

With 1,1,3,3-tetramethylguanidinium lactate; at 95 ℃; for 1h; Ionic liquid;

DOI:10.1007/s00706-012-0810-9

Reference yield: 88.0%

benzylurea (538-32-9) + ethyl 2-cyanoacetate (105-56-6) → 1-benzyl-6-aminouracil (41862-11-7)

Guidance literature:

With sodium ethanolate; In ethanol; Reflux;

DOI:10.1021/acs.jmedchem.7b00950

Reference yield: 70.0%

benzylurea (538-32-9) + cyanoacetic acid (372-09-8) → 1-benzyl-6-aminouracil (41862-11-7)

Guidance literature:

benzylurea; cyanoacetic acid; With acetic anhydride; at 75 - 80 ℃; for 2h;

In diethyl ether; at 20 ℃; for 1h;

With hydrogenchloride; sodium hydroxide; ethanol; water; more than 3 stages;

upstream raw materials:

benzylurea

cyanoacetic acid

1-benzyl-3-(2-cyanoacetyl)urea

ethyl 2-cyanoacetate

Downstream raw materials:

6-amino-1-benzyl-3-methyl uracil

6-amino-5-nitroso-1-(phenylmethyl)-2,4(1H,3H)-pyrimidinedione

N′-(3-benzyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-N,N-dimethylformimidamide

6-amino-1-benzyl-5-bromo-2,4(1H)-pyrimidinedione

Refernces

• 1、 Dzieszkowski, Krzysztof,Barańska, Izabela,Rafiński, Zbigniew. "Construction of Dihydropyrido[2,3- d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes". . p. 6645 - 6662. Retrieved 2020/07/14.
• 2、 Holschbach, Marcus H.,Bier, Dirk,Sihver, Wiebke,Schulze, Annette,Neumaier, Bernd. "Synthesis and Pharmacological Evaluation of Identified and Putative Metabolites of the A1 Adenosine Receptor Antagonist 8-Cyclopentyl-3-(3-fluoropropyl)-1-propylxanthine (CPFPX)". . p. 770 - 784. Retrieved 2017/05/26.