6-Amino-1-methyluracil

Base Information

• Chemical Name: 6-Amino-1-methyluracil
• CAS No.: 2434-53-9
• Molecular Formula: C5 H7 N3 O2
• Molecular Weight: 141.129
• Hs Code.: 29335990
• European Community (EC) Number: 219-422-3
• NSC Number: 7369
• DSSTox Substance ID: DTXSID30179076
• Nikkaji Number: J216.075G
• Wikidata: Q63408603
• ChEMBL ID: CHEMBL89725
• Mol file: 2434-53-9.mol

Synonyms:6-Amino-1-methyluracil;2434-53-9;6-amino-1-methylpyrimidine-2,4(1H,3H)-dione;1-methyl-6-Aminouracil;6-amino-1-methylpyrimidine-2,4-dione;MFCD00075366;2,4(1H,3H)-Pyrimidinedione, 6-amino-1-methyl-;6-amino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione;EINECS 219-422-3;6-Amino-1-methyl-1H-pyrimidine-2,4-dione;NSC7369;6-Amino-1-methyl-2,4(1H,3H)-pyrimidinedione;SCHEMBL31137;CHEMBL89725;AMY485;SCHEMBL5503560;6-Amino-1-methyluracil, 97%;DTXSID30179076;BCP04504;NSC 7369;NSC-7369;BBL036250;GEO-00177;STL249873;STL509326;AKOS000120920;AKOS025285888;AC-2045;BS-3799;CS-W016441;SB57246;SY049507;BB 0248355;FT-0620904;EN300-19845;H11262;1-Methyl-6-aminopyrimidine-2,4(1H,3H)-dione;6-amino-4-hydroxy-1-methylpyrimidin-2(1H)-one;6-Amino-1-methyl-2,4(1H,3H)-pyrimidinedione #;A852496;W-107329;Q63408603;F1967-1167;Z104475748

Chemical Property of 6-Amino-1-methyluracil

Chemical Property:

• Appearance/Colour: almost white to slightly beige crystalline powder
• Melting Point: 300 °C
• Refractive Index: 1.548
• PKA: 9.26±0.40(Predicted)
• PSA: 80.88000
• Density: 1.339 g/cm³
• LogP: -0.76300
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Soluble in diluted sodium hydroxide solution.
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 141.053826475
• Heavy Atom Count: 10
• Complexity: 221

Purity/Quality:

99%, ^*data from raw suppliers

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

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C(=CC(=O)NC1=O)N
• Uses: 6-Amino-1-methyluracil is known to exert inhibitory effects towards DNA repair glycosylase. It is also known to be used as a flame retardant. 6-Amino-1-methyluracil may be used in the preparation of 1,1?-di methyl-1H-spiro[pyrimido[4,5-b]quinoline-5,5?-pyrrolo[2,3-d]pyrimidine]-2,2?,4,4?,6?(1?H,3H,3?H,7?H,1?H)-pentaone, via reaction with isatin in the presence of catalytic p-toluene sulfonic acid.

Technology Process of 6-Amino-1-methyluracil

There total 11 articles about 6-Amino-1-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: 98.2%

ethyl 2-cyanoacetate (105-56-6) + N-Methylurea (598-50-5) → 6-amino-1-methyluracil (2434-53-9)

Guidance literature:

N-Methylurea; With sodium ethanolate; In ethanol; at 20 ℃; Reflux;

ethyl 2-cyanoacetate; In ethanol; for 5h; Reagent/catalyst; Solvent;

Reference yield: 87.0%

N-cyanoacetyl-N'-methyl-urea (6972-77-6) → 6-amino-1-methyluracil (2434-53-9)

Guidance literature:

With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; for 24h; Heating;

Reference yield: 70.0%

cyanoacetic acid (372-09-8) + N-Methylurea (598-50-5) → 6-amino-1-methyluracil (2434-53-9)

Guidance literature:

cyanoacetic acid; N-Methylurea; With acetic anhydride; at 60 ℃; for 0.166667h; microwave irradiation;

With sodium hydroxide; In ethanol; at 20 ℃;

DOI:10.1016/j.tetlet.2005.06.075

upstream raw materials:

4-Amino-2,6-dihydroxypyrimidine

methyl p-toluene sulfonate

dimethyl sulfate

N-cyanoacetyl-N'-methyl-urea

Downstream raw materials:

6-amino-1-methyl-5-phenylazo-1H-pyrimidine-2,4-dione

6-amino-1-methyl-3-propyl-1,3-dihydropyrimidine-2,4-dione

6-Amino-1,3-dimethylbarbituric acid

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

Refernces

• 1、 Devi, Ipsita,Bhuyan, Pulak J.. "An expedient method for the synthesis of 6-substituted uracils under microwave irradiation in a solvent-free medium". . p. 5727 - 5729. Retrieved 2005.
• 2、 -. "Preparation method of linagliptin for treating type II diabetes mellitus". Paragraph 0039-0054. . Retrieved 2021/03/30.
• 3、 Belter, Birgit,Caflisch, Amedeo,K?ckerling, Martin,Kinski, Elisa,Mamat, Constantin,Neuber, Christin,Pietzsch, Jens,Pretze, Marc,Steinbach, J?rg. "Synthesis, radiolabelling and initial biological characterisation of 18F-labelled xanthine derivatives for PET imaging of Eph receptors". . p. 3104 - 3116. Retrieved 2020/05/08.