2,5-Dichloro-3,4-dihydropyrimidin-4-one

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Cat Number

INT169557022

CAS Number

169557-02-2

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Product Detail Description Customer Q&A

CAS Number

169557-02-2

Synonyms

4(3H)-PyriMidinone, 2,5-dichloro-;2,5-dichloropyrimidin-4(3H)-one

Molecular Formula

C4H2Cl2N2O

Molecular Weight

164.98

Smiles

C1(Cl)=NC=C(Cl)C(=O)N1

Relative Density

1.76

pKa

4.6

General Description

2,5-Dichloro-3,4-dihydropyrimidin-4-one is a chlorinated dihydropyrimidinone featuring two chlorine atoms at the C-2 and C-5 positions of the pyrimidine ring. The C-4 carbonyl (lactam) and the 3,4-double bond (dihydropyrimidinone) provide multiple electrophilic sites for nucleophilic substitution, making this intermediate a versatile scaffold for constructing more complex dihydropyrimidinone (DHPM) derivatives with diverse pharmacological activities.

Mechanism of Action

2,5-Dichloro-3,4-dihydropyrimidin-4-one acts as a key intermediate in the synthesis of dihydropyrimidinone (DHPM) derivatives via nucleophilic aromatic substitution (SNAr) at the C-2 and C-5 positions. Amines, alkoxides, and thiolates readily displace the chloride ions, and the C-4 carbonyl can be transformed to thioamides, amidines, and other heterocycles. The DHPM scaffold is a privileged structure in medicinal chemistry, particularly for calcium channel modulators and antiviral agents.

Application

2,5-Dichloro-3,4-dihydropyrimidin-4-one is used as an intermediate in the synthesis of dihydropyrimidinone (DHPM) derivatives, a class of compounds with diverse pharmacological activities including calcium channel modulation, anti-tumor, anti-viral, and anti-inflammatory properties. The most notable therapeutic application is in the synthesis of Batrabin (a DHPM-based anticancer agent) and its analogs. It is also used in the construction of nucleoside mimetics.

What is the recommended storage condition for 2,5-Dichloro-3,4-dihydropyrimidin-4-one?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

What documentation is provided with each batch of 2,5-Dichloro-3,4-dihydropyrimidin-4-one?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

Is 2,5-Dichloro-3,4-dihydropyrimidin-4-one available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

What functional groups in 2,5-Dichloro-3,4-dihydropyrimidin-4-one are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

Is 2,5-Dichloro-3,4-dihydropyrimidin-4-one manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.