3289-53-0

Basic information

• Product Name: 6-AMINO-4-METHOXY-2-METHYLTHIOURACIL
• Synonyms: 6-AMINO-4-METHOXY-2-METHYLTHIOURACIL;4-Amino-6-methoxy-2-(methylthio)pyrimidine;6-Methoxy-2-(methylthio)-4-pyrimidinamine;6-Methoxy-2-(Methylthio)pyriMidin-4-aMine
• CAS NO: 3289-53-0
• Molecular Formula: C6H9N3OS
• Molecular Weight: 171.22
• EINECS: 604-604-1
• Product Categories: Chemical Amines;Amines;Bases & Related Reagents;Heterocycles;Nucleotides;Sulfur & Selenium Compounds
• Mol File: 3289-53-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 140-142°C
• Boiling Point: 357.4 °C at 760 mmHg
• Flash Point: 170 °C
• Appearance: Pale Yellow Crystalline Solid
• Density: 1.29 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Acetone, DMSO, Methanol
• PKA: 2.90±0.10(Predicted)
• CAS DataBase Reference: 6-AMINO-4-METHOXY-2-METHYLTHIOURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-4-METHOXY-2-METHYLTHIOURACIL(3289-53-0)
• EPA Substance Registry System: 6-AMINO-4-METHOXY-2-METHYLTHIOURACIL(3289-53-0)

Safety Data

• Hazardous Substances Data: 3289-53-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Crystalline Solid

Uses

4-Alkoxy-6-aminopyrimidine derivative

Upstream product

• 1004-40-6 6-Amino-2-thiouracil 
• 77-78-1 dimethyl sulfate 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 186380-87-0 6-amino-2-methylthiopyrimidin-4(3H)-one 
• 1074-41-5 2-(Methylthio)-4-hydroxy-6-aminopyrimidine 
• 1005-38-5 4-amino-6-chloro-2-methylthiopyrimidine 

Downstream Products

• 696-45-7 4-amino-6-methoxypyrimidine 
• 6128-06-9 6-methoxypyrimidin-4(3H)-one 
• 178878-19-8 Hg2(4-amino-6-methoxy-2-methylthiopyrimidine)2(μ-Cl)2Cl2 

Relevant articles and documents

Tunable Push-Pull Interactions in 5-Nitrosopyrimidines

The effect of push-pull interactions in a series of variously substituted 5-nitrosopyrimidines on the strength of intramolecular hydrogen bonds, the height of rotational barriers around formally single bonds, UV-vis spectra and electrochemical behavior is explored. Intramolecular charge transfer (ICT) leads to a shift of electron density from electron-donating substituents, which is readily observable by NMR spectroscopy. The 5-nitroso group is able to form strong intramolecular hydrogen bonds with neighboring amino substituents. As a result, two rotamers with reversed orientation of the 5-nitroso group are observed for compounds with two different hydrogen-bond donors in neighboring positions. The barriers of interconversion between the two rotamers are strongly influenced by ICT, whereas the ratio of such rotamers depends primarily on the character of the hydrogen-bond donors. The ICT also significantly affects the position of UV-vis absorption maxima, which can be tuned in a broad range of 100 nm by the selection of appropriate substituents. Finally, ICT influences oxidation potential of the 5-nitrosopyrimidines and the stability of the resulting nitroso radical cations, the structures of which are determined by EPR spectroscopy.

Novel procedure for selective C-nitrosation of aminopyrimidine derivatives under neutral conditions. Scope and synthetic applications

A novel simple method, based on treatment with isoamyl nitrite (IAN) in DMSO without any added acid, to produce selective C(5)-nitrosation of aminopyrimidine derivatives is described. It proved to be suitable for a multigram scale and applicable to a larger range of pyrimidine derivatives, including amino-dialkoxypyrimidines, than the procedures previously known. Its scope is analyzed and some example on the usefulness of the newly prepared substances as intermediates in the synthesis of fused heterobicyclic derivatives of potential biological interest is presented.