6-chloro-1,3-dimethyluracil is an important pharmaceutical intermediate and belongs to uracil derivatives. Its molecular structure not only retains the pharmaceutical active core of pyrimidine ring, but also introduces functional groups such as chlorine group and methyl group, which makes it a intermediates in pharmaceutical with great development value. In the field of medicine, it can be used as the core structure mother nucleus of antiviral, antibacterial and antitumor drugs, and can also be further derivatized to synthesize a variety of drug molecules with specific functions. In this paper, the molecular characteristics, synthesis methods and main applications of 6-chloro-1,3-dimethyluracil as pharma intermediates will be comprehensively discussed.
Molecular Characteristics of 6-Chloro-1,3-Dimethyluracil
Molecular Structure
Pyrimidine ring core: The pyrimidine ring of 6-chloro-1,3-dimethyluracil is the basic unit in nucleic acid and plays an important role in intracellular metabolism.
Chlorine substituent: located at the 6 th position of pyrimidine ring, it provides high chemical reactivity and can generate a series of functional derivatives through nucleophilic substitution reaction.
Methyl group: the substitution of methyl groups at positions 1 and 3 improves the liposolubility of molecules, thus improving the absorption and metabolism of drugs.
Chemical Property
6-chloro-1,3-dimethyluracil has the following chemical characteristics:
Activity of nucleophilic substitution reaction: chlorine atom is a good leaving group, which is easy to substitute with nucleophilic reagents such as amino, mercaptan or alcohol.
Stability: The compound has high chemical stability to light, heat and acid-base conditions, and is suitable for large-scale industrial production and storage.
Synthesis Method of 6-Chloro-1,3-Dimethyluracil
The synthesis of 6-chloro-1,3-dimethyluracil is usually divided into two steps: the construction of pyrimidine ring and chlorination reaction.
Construction of pyrimidine ring
Urea and malonamide (or its derivatives) form uracil skeleton through condensation reaction. Under the action of acidic or alkaline catalyst, 1,3- dimethyluracil can be produced by high temperature heating and solvent regulation.
Chlorination reaction
Selection of chlorinating agent: Usually thionyl chloride (SOCl₂), phosphoryl chloride (POCl₃) or chlorine gas is used as chlorinating agent.
Reaction conditions: control the reaction temperature (50-80℃) and the dosage of chlorinating agent to improve selectivity and reduce by-products.
Post-treatment: high purity 6-chloro-1,3-dimethyluracil can be obtained by recrystallization or column chromatography purification.
Process optimization
Using anhydrous solvent (such as dichloromethane or tetrahydrofuran) as reaction medium can significantly improve the product yield.
Through catalyst optimization and reaction equipment upgrading, green and large-scale production can be realized.