6-Amino-4-methoxy-2-methylthiouracil

Base Information

• Chemical Name: 6-Amino-4-methoxy-2-methylthiouracil
• CAS No.: 3289-53-0
• Molecular Formula: C₆H₉N₃OS
• Molecular Weight: 171.223
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID30399550
• Wikidata: Q72438768
• Mol file: 3289-53-0.mol

Synonyms:6-Amino-4-methoxy-2-methylthiouracil;3289-53-0;6-Methoxy-2-(methylthio)pyrimidin-4-amine;6-methoxy-2-methylsulfanylpyrimidin-4-amine;6-METHOXY-2-(METHYLSULFANYL)PYRIMIDIN-4-AMINE;SCHEMBL8721091;DTXSID30399550;FBAYMIJHPUCRMU-UHFFFAOYSA-N;AKOS006277542;SB55795;6-amino-4-methoxy-2-methylthiopyrimidine;2-methylmercapto-4-amino-6-methoxypyrimidine;CS-0361032;FT-0661881;6-methoxy-2-(methylsulfanyl)-4-pyrimidinylamine;AE-848/01533038;J-018923

Chemical Property of 6-Amino-4-methoxy-2-methylthiouracil

Chemical Property:

• Appearance/Colour: Pale Yellow Crystalline Solid
• Melting Point: 140-142°C
• Boiling Point: 357.4 °C at 760 mmHg
• PKA: 2.90±0.10(Predicted)
• Flash Point: 170 °C
• PSA: 86.33000
• Density: 1.29 g/cm³
• LogP: 1.37050
• Storage Temp.: Refrigerator
• Solubility.: Acetone, DMSO, Methanol
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 171.04663309
• Heavy Atom Count: 11
• Complexity: 124

Purity/Quality:

98%Min ^*data from raw suppliers

6-Amino-4-methoxy-2-methylthiouracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=NC(=NC(=C1)N)SC
• Uses: 4-Alkoxy-6-aminopyrimidine derivative

Technology Process of 6-Amino-4-methoxy-2-methylthiouracil

There total 8 articles about 6-Amino-4-methoxy-2-methylthiouracil 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: 91.0%

sodium methylate (124-41-4) + 4-amino-6-chloro-2-methylthiopyrimidine (1005-38-5) → 6-methoxy-2-methylsulfanyl-pyrimidin-4-ylamine (3289-53-0)

Guidance literature:

In methanol; for 72h; Reflux;

DOI:10.1021/acs.joc.6b00446

Reference yield: 27.0%

2-(Methylthio)-4-hydroxy-6-aminopyrimidine (1074-41-5) + methyl iodide (74-88-4) → 6-methoxy-2-methylsulfanyl-pyrimidin-4-ylamine (3289-53-0) + 6-amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (54030-56-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 - 85 ℃; for 4h;

DOI:10.1021/jm701159t

Reference yield:

dimethyl sulfate (77-78-1) → 6-methoxy-2-methylsulfanyl-pyrimidin-4-ylamine (3289-53-0)

Guidance literature:

With potassium hydroxide;

upstream raw materials:

6-Amino-2-thiouracil

dimethyl sulfate

sodium methylate

methyl iodide

Downstream raw materials:

4-amino-6-methoxypyrimidine

Hg2(4-amino-6-methoxy-2-methylthiopyrimidine)2(μ-Cl)2Cl2

6-methoxypyrimidin-4(3H)-one

Refernces

• 1、 Cosimelli, Barbara,Greco, Giovanni,Ehlardo, Marina,Novellino, Ettore,Da Settimo, Federico,Taliani, Sabrina,La Motta, Concettina,Bellandi, Marusca,Tuccinardi, Tiziano,Martinelli, Adriano,Ciampi, Osele,Trincavelli, Maria Letizia,Martini, Claudia. "Derivatives of 4-amino-6-hydroxy-2-mercaptopyrimidine as novel, potent, and selective A3 adenosine receptor antagonists". . p. 1764 - 1770. Retrieved 2008/12/22.
• 2、 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.