2-Chloro-4-[3-iodo-1-(1-methylethyl)-1H-pyrazol-4-yl]pyrimidine
[CAS# 1269440-58-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 2-Chloro-4-[3-iodo-1-(1-methylethyl)-1H-pyrazol-4-yl]pyrimidine
• Molecular Formula: C₁₀H₁₀ClIN₄
• Molecular Weight: 348.57
• CAS Registry Number: 1269440-58-5
• EC Number: 826-697-9
• SMILES: CC(C)N1C=C(C(=N1)I)C2=NC(=NC=C2)Cl

Properties

• Solubility: Very slightly soluble (0.12 g/L) (25 ºC), Calc.^*
• Density: 1.86±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.717, Calc.^*
• Boiling Point: 469.8±40.0 ºC (760 mmHg), Calc.^*
• Flash Point: 238.0±27.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H303-H317-H401-H411
• Precautionary Statements: P261-P272-P273-P280-P301+P317-P302+P352-P321-P333+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H401
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	5	H303
Skin sensitization	Skin Sens.	1	H317

Discovory and Applicatios

2-Chloro-4-[3-iodo-1-(1-methylethyl)-1H-pyrazol-4-yl]pyrimidine represents a significant advancement in the field of heterocyclic chemistry, primarily due to its versatile application in pharmaceuticals and agrochemicals. This compound falls under the category of pyrazolopyrimidines, a class known for their bioactivity and role as kinase inhibitors. The introduction of halogens, specifically iodine and chlorine, enhances the compound's reactivity, facilitating subsequent functionalization in complex synthetic pathways.

The initial discovery of 2-Chloro-4-[3-iodo-1-(1-methylethyl)-1H-pyrazol-4-yl]pyrimidine was driven by the need for selective inhibitors targeting oncogenic pathways. This compound was identified as a core scaffold in the development of tyrosine kinase inhibitors, contributing to advancements in cancer therapy. The structural features allow for high binding affinity to ATP-binding sites, thus effectively modulating enzymatic activity in malignant cells.

Synthesis of this compound typically involves a stepwise construction, starting with pyrazole formation followed by selective halogenation and pyrimidine coupling. A notable method employs N-iodosuccinimide (NIS) for regioselective iodination of pyrazoles, followed by chlorination at the pyrimidine ring using phosphorus oxychloride (POCl3). This approach not only ensures high yield but also provides a scalable route for industrial applications.

Applications of 2-Chloro-4-[3-iodo-1-(1-methylethyl)-1H-pyrazol-4-yl]pyrimidine extend beyond oncology. The compound demonstrates potential in agrochemical development, acting as a core structure for herbicides and fungicides. Its inhibitory effects on key enzymes within plant pathogens highlight its utility in improving crop resilience and yield.