7153-13-1

Basic information

• Product Name: 2-Amino-4,6-dichloro-5-methylpyrimidine
• Synonyms: 4,6-dichloro-5-methylpyrimidin-2-amine;4,6-DICHLORO-5-METHYLPYRIMIDINE-2-AMINE;2-Amino-4,6-dichloro-5-methylpyrimidine;(4,6-dichloro-5-methyl-pyrimidin-2-yl)amine
• CAS NO: 7153-13-1
• Molecular Formula: C₅H₅Cl₂N₃
• Molecular Weight: 178.02
• EINECS: 200-582-5
• Product Categories: APIs & Intermediate;Pyrimidine;Pyrimidines;Heterocycle-Pyrimidine series
• Mol File: 7153-13-1.mol

Chemical Properties

• Boiling Point: 354.1 °C at 760 mmHg
• Flash Point: 168 °C
• Appearance: /
• Density: 1.504 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.55±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-4,6-dichloro-5-methylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4,6-dichloro-5-methylpyrimidine(7153-13-1)
• EPA Substance Registry System: 2-Amino-4,6-dichloro-5-methylpyrimidine(7153-13-1)

Safety Data

• Hazardous Substances Data: 7153-13-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4,6-dichloro-5-methylpyrimidine is used as a pharmaceutical intermediate for its unique medicinal properties. Its heterocyclic aromatic structure allows it to serve as a key component in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapies.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-Amino-4,6-dichloro-5-methylpyrimidine is utilized for its potential in the synthesis of novel compounds with therapeutic applications. Its structural features make it a valuable building block in the creation of new molecules with potential medicinal uses.
Used in Biochemistry:
2-Amino-4,6-dichloro-5-methylpyrimidine is employed in biochemistry for its role in the study of biological processes and the development of bioactive molecules. Its unique structure and properties facilitate research into the interactions of pyrimidine derivatives with biological systems, potentially leading to advancements in our understanding of cellular mechanisms and the design of new bioactive compounds.
Used in Chemical Research and Development:
2-Amino-4,6-dichloro-5-methylpyrimidine is used as a research compound in chemical studies, where its properties and reactivity are explored for potential applications in various fields. Its synthesis and modification through chemical reactions can lead to the discovery of new compounds with diverse applications, including but not limited to the medical and pharmaceutical industries.

Upstream product

• 55477-35-5 2-amino-4,6-dioxy-5-methylpyridine 
• 10025-87-3 trichlorophosphate 
• 1395342-96-7 4,6-dichloro-5-methyl-2-{[(dimethylamino)methylene]amino}pyrimidine 
• 6627-65-2 2-amino-4,6-dihydroxy-5-methylpyrimidine 

Downstream Products

• 18588-37-9 5-methylpyrimidine-2,4-diamine 
• 774607-97-5 2-amino-4-chloro-6-(5-chloro-2-methoxyphenyl)-5-methyl-pyrimidine 
• 77378-84-8 4-chloro-5-methyl-6-phenylpyrimidin-2-amine 

Relevant articles and documents

5-substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4, 6-dichloropyrimidines: Synthesis and inhibitory effects on immune-activated nitric oxide production

A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino- 4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6- dichloropyrimidine with an IC50 of 2 μM (higher activity than the most potent reference compound) while the IC50s of other derivatives were within the range of 9-36 l M. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.

5-Substituted 2-amino-4, 6-dihydroxypyrimidines and 2-amino-4, 6-dichloropyrimidines: Synthesis and inhibitory effects on immune-activated nitric oxide production

A series of 5-substituted 2-amino-4, 6-dihydr-oxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4, 6-dihydroxypyrimi-dine analogs to novel 5-substituted 2-amino-4, 6-dichloro-pyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino-4, 6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4, 6-dichloropyrimidine with an IC50 of 2 lM (higher activity than the most potent reference compound) while the IC50s of other derivatives were within the range of 9-36 μM. The 2-amino-4, 6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.

PYRIMIDINE COMPOUNDS INHIBITING THE FORMATION OF NITRIC OXIDE AND PROSTAGLANDIN E2, METHOD OF PRODUCTION THEREOF AND USE THEREOF

The invention provides pyrimidine compounds of general formula (I), which reduce simultaneously the production of nitric oxide (NO) and prostaglandin E2 (PGE2). They have no negative effect on the viability of cells in concentrations decreasing the production of these factors by up to 50%; they are not cytotoxic. Furthermore, a method of preparation of the pyrimidine compounds of general formula (I), carrying 2-formamido group, a pharmaceutical composition comprising the substituted pyrimidine compounds according to the invention, and the use of these compounds for the treatment of inflammatory and cancer diseases are provided.˙

Structure-activity studies on a series of a 2-aminopyrimidine-containing histamine H4 receptor ligands

A series of 2-aminopyrimidines was synthesized as ligands of the histamine H4 receptor (H4R). Working in part from a pyrimidine hit that was identified in an HTS campaign, SAR studies were carried out to optimize the potency, which led to compound 3,4-tert-butyl-6-(4-methylpiperazin-1-yl) pyrimidin-2-ylamine. We further studied this compound by systematically modifying the core pyrimidine moiety, the methylpiperazine at position 4, the NH2 at position 2, and positions 5 and 6 of the pyrimidine ring. The pyrimidine 6 position benefited the most from this optimization, especially in analogs in which the 6-tert-butyl was replaced with aromatic and secondary amine moieties. The highlight of the optimization campaign was compound 4,4-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]benzonitrile, which was potent in vitro and was active as an anti-inflammatory agent in an animal model and had antinociceptive activity in a pain model, which supports the potential of H4R antagonists in pain.

Pyrimidines and uses thereof

The invention relates to pyrimidines and uses thereof, including to inhibit lysophosphatidic acid acyltransferase β (LPAAT-β) activity and/or proliferation of cells such as tumor-cells.