73-70-1

Basic information

• Product Name: 4-Pyrimidinamine, 2,5-dimethyl- (9CI)
• Synonyms: 4-Pyrimidinamine, 2,5-dimethyl- (9CI);2,5-Dimethyl-4-pyrimidineamine;4-Amino-2,5-dimethylpyrimidine;4-PyriMidinaMine, 2,5-diMethyl-;2,5-DiMethyl-4-pyriMidinaMine;[1,3]Thiazolo[5,4-C]Pyridinre
• CAS NO: 73-70-1
• Molecular Formula: C₆H₉N₃
• Molecular Weight: 123.15576
• Product Categories: PYRIMIDINE
• Mol File: 73-70-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 4-Pyrimidinamine, 2,5-dimethyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pyrimidinamine, 2,5-dimethyl- (9CI)(73-70-1)
• EPA Substance Registry System: 4-Pyrimidinamine, 2,5-dimethyl- (9CI)(73-70-1)

Safety Data

• Hazardous Substances Data: 73-70-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Pyrimidinamine, 2,5-dimethyl(9CI) is used as a synthetic intermediate for the preparation of hydroxypyrimidine complexes with palladium. These complexes play a crucial role in the synthesis of heteroarene compounds, which are essential building blocks in the development of pharmaceuticals with diverse therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 4-Pyrimidinamine, 2,5-dimethyl(9CI) serves as a valuable precursor for the synthesis of various heterocyclic compounds. Its unique structure allows for the exploration of new chemical reactions and the development of novel compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 18260-92-9 6-chloro-2,5-dimethyl-pyrimidin-4-ylamine 
• 100368-38-5 β-ethoxy-β-methoxy-isobutyronitrile 
• 124-42-5 acetamidine hydrochloride 
• 3059-71-0 2,5-dimethyl-3H-pyrimidin-4-one 
• 47494-29-1 2-(1-hydroxybenzyl)thiamin kation 
• 857412-07-8 2,5-dimethyl-1H-pyrimidine-4,6-dione 
• 1780-33-2 4,6-dichloro-2,5-dimethyl-pyrimidine 
• 100-52-7 benzaldehyde 

Downstream Products

• 1351515-92-8 3-amino-2,5-dimethylpyrimidin-4(3H)-iminium 2,4,6-trimethylbenzenesulfonate 

Relevant articles and documents

The Need for an Alternative to Radicals as the Cause of Fragmentation of a Thiamin-Derived Breslow Intermediate

Mandelylthiamin (1) is a conjugate of benzoylformate and thiamin that loses CO2 to form the classic Breslow intermediate (2), whose expected fate is formation of the thiamin conjugate of benzaldehyde (3). Surprisingly, it was observed that 2 decomposes to 4 and 5 and rearranges to 6 in competition with the expected protonation to give 3. Recent reports propose that the alternatives to protonation arise from homolysis followed by radical-centered processes. It is now found, instead, that the spectroscopic observations cited in support of the proposed radical pathways are likely to be the result of other events. An alternative explanation is that ionization of the enolic hydroxy group of 2 and resultant electronic reorganization leads to C?C bond cleavage and non-radical intermediates that readily form 4, 5, and 6.

HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes

Reactivity of intermediates in benzoylformate decarboxylase: Avoiding the path to destruction

Benzoylformate decarboxylase forms a covalent intermediate from thiamin diphosphate (TDP) and benzoylformate, α-mandelylTDP. This loses carbon dioxide to form a carbanion (enamine). Protonation of the carbanion and elimination of benzaldehyde regenerate e

Decomposition of 2-(1-hydroxybenzyl) thiamin in neutral aqueous solutions: benzaldehyde and thiamin are not the products

It has been reported that in neutral aqueous solutions, the adduct of benzaldehyde and thiamin, 2-(l-hydroxybenzyl)thiamin, HBzT (2), undergoes general base-catalyzed reversion to thiamin and benzaldehyde (E. J. Crane, III, and M. W. Washabaugh (1991) Bioorg. Chem.19, 351). An unusual mechanism had been invoked to explain the kinetic observations. In the present study, it is shown that in solutions of pH 8, HBzT fragments at the bridge methylene group to 2,5-dimethyl-4-amino-pyrimidine (3) and 2-benzoyl-5-(2-hydroxyethyl)-4-methylthiazole (4), not thiamin and benzaldehyde (which are the products at higher pH) (Scheme 3). Buffer catalysis is not observed where the products are thiamin and benzaldehyde. In neutral solution under conditions in which the products are 3 and 4, the reaction is general base-catalyzed. It is likely that catalysis assists the cleavage of the methylene bridge. Mechanistic proposals based on the elimination of benzaldehyde from HBzT in neutral and acidic solutions should be reconsidered. Copyright