1606-49-1

Basic information

• Product Name: 1,4,5,6-TETRAHYDROPYRIMIDINE
• Synonyms: 1,4,5,6-TETRAHYDROPYRIMIDINE;NSC 72087;1,4,5,6-Tetrahydropyrimidine 97%
• CAS NO: 1606-49-1
• Molecular Formula: C₄H₈N₂
• Molecular Weight: 84.12
• Product Categories: Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Nucleotides;Building Blocks;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 1606-49-1.mol

Chemical Properties

• Melting Point: 88-89 °C
• Boiling Point: 88-89 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Viscous colorless liquid
• Density: 1.024 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00785mmHg at 25°C
• Refractive Index: n20/D 1.5194(lit.)
• PKA: 12.21±0.20(Predicted)
• CAS DataBase Reference: 1,4,5,6-TETRAHYDROPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,5,6-TETRAHYDROPYRIMIDINE(1606-49-1)
• EPA Substance Registry System: 1,4,5,6-TETRAHYDROPYRIMIDINE(1606-49-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 1606-49-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,4,5,6-Tetrahydropyrimidine is used as a building block for the synthesis of various pharmaceutical agents, particularly derivatives that can act as neuromuscular blocking, cardiovascular, and antidepressant agents. These derivatives have the potential to improve the treatment of various medical conditions by targeting specific physiological pathways.
Used in Environmental Applications:
1,4,5,6-Tetrahydropyrimidine is used as a carbon dioxide fixation agent for its ability to react with CO2 and form a zwitterionic adduct. This property can be utilized in environmental applications, such as carbon capture and storage, to help mitigate the effects of climate change by reducing the amount of CO2 released into the atmosphere.
Used in Chemical Research:
1,4,5,6-Tetrahydropyrimidine serves as an important compound in chemical research, particularly in the development of new materials and compounds with specific properties. Its unique reactivity with carbon dioxide and its potential applications in various industries make it a valuable subject of study for chemists and material scientists.

InChI:InChI=1/C4H8N2/c1-2-5-4-6-3-1/h4H,1-3H2,(H,5,6)

Upstream product

• 289-95-2 PYRIMIDINE 
• 290-87-9 1,3,5-Triazine 
• 109-76-2 Trimethylenediamine 
• 22536-67-0 2,5-dichloropyrimidine 
• 109-94-4 formic acid ethyl ester 
• 201230-82-2 carbon monoxide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 122-51-0 orthoformic acid triethyl ester 
• 7647-01-0 hydrogenchloride 
• 3934-20-1 2,6-Dichloropyrimidine 
• 60-29-7 diethyl ether 
• 7732-18-5 water 
• 1443453-33-5 1,4,5,6-Tetrahydropyrimidinium bicarbonate 

Downstream Products

• 111-33-1 1,3-bis(methylamino)propane 
• 77891-10-2 1-Tosyl-1,4,5,6-tetrahydropyrimidin 
• 883991-82-0 (2S,4S)-2-{[(5,6-Dihydro-4H-pyrimidin-1-yl)-imino-methyl]-carbamoyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester 
• 468741-36-8 5-(1,4,5,6-tetrahydropyrimidin-1-yl)-3-methyl-2-nitro aniline 
• 301672-56-0 2-Chloro-5-[(5,6-dihydro-1(4H)-pyrimidinyl)methyl]-N-(tricyclo[3.3.1.13.7]dec-1-ylmethyl)-benzamide 
• 123579-64-6 1-(3-Phenyl-3-cyclohexyl-3-hydroxy)propyl-1,4,5,6-tetrahydropyrimidine hydrochloride 
• 1403678-41-0 N-1-[1-(2,6-diisopropylphenylimino)ethyl]-4,5,6-trihydropyrimidine 

Relevant articles and documents

Fast equilibrium of zwitterionic adduct formation in reversible fixation-release system of CO2 by amidines under dry conditions

We investigated the fixation of CO2 by several amidines in solution and found that simple monocyclic amidines fixed CO2 under dry conditions to quantitatively afford the corresponding bicarbonates through hydrolysis of the zwitterion

PRODUCTION METHOD OF CYCLIC COMPOUND

PROBLEM TO BE SOLVED: To provide an industrially simple production method of a cyclic compound. SOLUTION: A production method of a cyclic compound includes a step to obtain a reduced form (B) by reducing an unsaturated bond in a ring structure of an aromatic compound (A) by means of catalytic hydrogenation of the aromatic compound (A) or its salt using palladium carbon as a catalyst under a normal pressure, in which the aromatic compound (A) has one or more ring structures selected from a group consisting of a five membered-ring, a six membered-ring, and a condensed ring of the five membered-ring or the six membered-ring with another six membered-ring, a hetero atom can be included in the ring structure, and the aromatic compound (A) can have one or two side chains bonded to the ring structure and does not have any carbon-carbon triple bond in the side chain. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?

Hydrogenation of over a dozen aromatic compounds, including both heteroarenes and arenes, over palladium on carbon (Pd/C, 1–100 molpercent) with H2-balloon pressure at room temperature is reported. Analyses using pyridine as a model substrate revealed that acetic acid was the best solvent, as using only 1 molpercent Pd/C provided piperidine quantitatively. Substrate scope analysis and density functional theory calculations indicated that reaction rates are highly dependent on frontier molecular orbital characteristics and the steric bulkiness of substituents. Moreover, the established method was used for the concise synthesis of the anti-Alzheimer drug donepezil (Aricept?).

Hydrogenation of N-Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters

A rhodium-catalyzed method for the hydrogenation of N-heteroarenes is described. A diverse array of unsubstituted N-heteroarenes including pyridine, pyrrole, and pyrazine, traditionally challenging substrates for hydrogenation, were successfully hydrogenated using the organometallic precatalysts, [(η5-C5Me5)Rh(N-C)H] (N-C = 2-phenylpyridinyl (ppy) or benzo[h]quinolinyl (bq)). In addition, the hydrogenation of polyaromatic N-heteroarenes exhibited uncommon chemoselectivity. Studies into catalyst activation revealed that photochemical or thermal activation of [(η5-C5Me5)Rh(bq)H] induced C(sp2)-H reductive elimination and generated the bimetallic complex, [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H]. In the presence of H2, both of the [(η5-C5Me5)Rh(N-C)H] precursors and [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H] converted to a pentametallic rhodium hydride cluster, [(η5-C5Me5)4Rh5H7], the structure of which was established by NMR spectroscopy, X-ray diffraction, and neutron diffraction. Kinetic studies on pyridine hydrogenation were conducted with each of the isolated rhodium complexes to identify catalytically relevant species. The data are most consistent with hydrogenation catalysis prompted by an unobserved multimetallic cluster with formation of [(η5-C5Me5)4Rh5H7] serving as a deactivation pathway.

Selective hydrogenation of N-heterocyclic compounds using Ru nanocatalysts in ionic liquids

N-Heterocyclic compounds have been tested in the selective hydrogenation catalysed by small 1-3 nm sized Ru nanoparticles (NPs) embedded in various imidazolium based ionic liquids (ILs). Particularly a diol-functionalised IL shows the best performance in the hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline (1THQ) with up to 99% selectivity.

1-(3-Nitrobenzenesulfonyl)-3,4-dimethylimidazolinium iodide: A more active tetrahydrofolate coenzyme model

Reaction of tetrahydrofolate coenzyme model, 1-(3-nitrobenzenesulfonyl)-3,4-dimethylimidazolinium iodide (2) with a series of aromatic amines produced N,N,N′-trisubstituted-2-methylethylenediamine derivatives (3-7). Reaction of the model with indole or carbazole in the presence of NaH provides two imidazolidine derivatives. The action of one-carbon transfer of the model with several bifunctional nucleophiles is also tested.

A general and efficient method for synthesis of functionalized ethylenediamine derivatives

Reaction of tetrahydrofolate model, 1-tosyl-3,4-dimethylimidazolinium iodide (1), and a series of aromatic or aliphatic amines produced N,N,N′-trisubstituted-2-methylethylenediamine derivatives (2-10) in good to excellent yields through a nucleophilic addition and the followed ring-opening mechanism. The coenzyme model was proved to be more electrophilic than those reported before.

A synthesis and properties of 1-substituted 1,4,5,6-tetrahydropyrimidines

The condensation of 1-substituted 1,3-diaminopropane with N,N-dimethyl-formamide dimethylacetal gives 1-alkyl- or aryl-1,4,5,6-tetrahydropyrimidines (2) and (3). Alkylation of the tetrahydropyrimidine derivatives with alkyl halides produces the 1,3-dialkyltetrahydropyrimidinium salts (4 and 5). The attempted dehydrogenation of 2 with sulfur leads to insertion of sulfur on the molecule.

CATALYTIC SYNTHESIS OF DIAZINES FROM 1,3-DIAMINOPROPANE AND 3-AMINO-1-PROPANOL

The transformation of 1,3-diaminopropane and 3-amino-1-propanol under pulse conditions over tungsten trioxide in an inert atmosphere at 300-500 deg C were investigated.The transformation of 1,3-diaminopropane leads to the formation of saturated pyrimidine

CARBONYLATION OF AMINES AND DIAMINES CATALYZED BY NICKEL CARBONYL

The carbonylation of amines and diamines was carried out using nickel carbonyl as the catalyst. reaction of butylamine, diethylamine, and diphenylamine with carbon monoxide all lead exclusively to the corresponding formamide derivative.Benzylamine reacts with carbon monoxide to yield urea and 1,2-diphenylethane.Diamines such as ethylenediamine, 1,2-diaminopropane, and 1,3-propylenediamine react to yield a cyclic condensation product, a cyclic uren, and a carbamic acid.