1-[2-(3,4-Dimethoxyphenyl)ethyl]-1,3-diazinane-2,4,6-trione CAS No. 75535-95-4

Product Description

1-[2-(3,4-Dimethoxyphenyl)ethyl]-1,3-diazinane-2,4,6-trione features a barbituric acid core, specifically a 1,3-diazinane-2,4,6-trione ring, with a 2-(3,4-dimethoxyphenyl)ethyl group attached to the nitrogen at the N-1 position. The presence of two methoxy groups (–OCH₃) on the aromatic ring enhances its lipophilicity and potential biological activity. It is synthesized through alkylation of barbituric acid with 2-(3,4-dimethoxyphenyl)ethyl bromide or via a Mannich-type reaction involving the phenethylamine derivative. Historically, barbiturates have been used as sedatives and hypnotics, and the 3,4-dimethoxyphenethyl moiety is found in some bioactive molecules. In research settings, it may serve as a chemical intermediate or building block for synthesizing other molecules.

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Product Use & Characteristics

Properties and Characteristics

Molecular Formula: C₁₄H₁₆N₂O₅
Molecular Weight: 292.29 g/mol
CAS Number: 75535-95-4
IUPAC Name: 1-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-diazinane-2,4,6-trione
Synonyms:

• 1-(3,4-Dimethoxyphenethyl)pyrimidine-2,4,6(1H,3H,5H)-trione

• Cambridge id 6943664

• 9QR3EJ78HM

Physical Form: Solid
Storage Conditions: Refrigerator
Purity: 0.98
Shipping Temperature: Room Temperature

Structure:

• Core Structure: 1-[2-(3,4-Dimethoxyphenyl)ethyl]-1,3-diazinane-2,4,6-trione features a pyrimidine-2,4,6-trione (barbituric acid) core, which is a six-membered heterocyclic ring with three carbonyl groups at positions 2, 4, and 6.

• Substituents: A 2-(3,4-dimethoxyphenyl)ethyl group is attached to the nitrogen atom at position 1 of the core. This group consists of an ethyl chain (–CH₂–CH₂–) attached to a phenyl ring with two methoxy groups (–OCH₃) at the 3 and 4 positions.

Key Features:

• Barbituric Acid Core: The diazinane ring contains three carbonyl groups, making it a barbiturate derivative.

• 3,4-Dimethoxyphenethyl Substituent: The aromatic ring has two methoxy groups (–OCH₃) at the 3 and 4 positions, contributing to its lipophilicity and potential biological activity.

• Solubility: Likely polar due to the uracil core and methoxy groups.

Uses

Medicinal Chemistry:

• Potential Pharmacological Relevance: 1-[2-(3,4-Dimethoxyphenyl)ethyl]-1,3-diazinane-2,4,6-trione may be relevant in medicinal chemistry studies, particularly as an analog or precursor of central nervous system depressants such as barbiturates.

• Neurological Agent: The 3,4-dimethoxyphenethyl group is seen in some bioactive molecules, suggesting potential use as a neurological agent.

• Drug Development: It could serve as a precursor for drug development, related to barbiturates or xanthine derivatives.

Research and Development:

• Chemical Intermediate: 1-[2-(3,4-Dimethoxyphenyl)ethyl]-1,3-diazinane-2,4,6-trione can be used as a chemical intermediate or building block for the synthesis of other molecules.

• Drug Impurity Research: It is often used in drug impurity studies.

Synthesis Methods

Alkylation:

• Alkylation of Barbituric Acid: 1-[2-(3,4-Dimethoxyphenyl)ethyl]-1,3-diazinane-2,4,6-trione was probably synthesized by alkylation of barbituric acid with 2-(3,4-dimethoxyphenyl)ethyl bromide or chloride under alkaline conditions.

Mannich-Type Reaction:

• Condensation with Phenethylamine Derivative: Alternatively, it can be synthesized via a Mannich-type reaction involving the phenethylamine derivative.

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