19646-06-1

Basic information

• Product Name: 4,6-DIIODOPYRIMIDINE
• Synonyms: 4,6-Diiodo-1,3-diazine
• CAS NO: 19646-06-1
• Molecular Formula: C₄H₂I₂N₂
• Molecular Weight: 331.88
• Product Categories: alkyl Iodine
• Mol File: 19646-06-1.mol

Chemical Properties

• Boiling Point: 333.883 °C at 760 mmHg
• Flash Point: 155.727 °C
• Appearance: /
• Density: 2.765 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.737
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -3.02±0.17(Predicted)
• CAS DataBase Reference: 4,6-DIIODOPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DIIODOPYRIMIDINE(19646-06-1)
• EPA Substance Registry System: 4,6-DIIODOPYRIMIDINE(19646-06-1)

Safety Data

• Hazardous Substances Data: 19646-06-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
4,6-DIIODOPYRIMIDINE is used as a key building block for the synthesis of various pharmaceutical drugs, leveraging its unique structure and reactivity. Its presence in drug molecules can enhance their therapeutic properties, such as antimicrobial and antiviral activities, making it a valuable component in the creation of new medications.
Used in Organic Synthesis:
In the field of organic synthesis, 4,6-DIIODOPYRIMIDINE is utilized as a reagent for the preparation of novel compounds. Its ability to participate in a variety of chemical reactions allows for the creation of new chemical entities with potential applications in various industries.
Used in the Preparation of Iodinated Pyrimidine Derivatives:
4,6-DIIODOPYRIMIDINE is employed in the synthesis of iodinated pyrimidine derivatives, which have a wide range of applications. These derivatives can be used in the development of contrast agents for medical imaging, as well as in other specialized applications within the chemical and pharmaceutical sectors.
Used in Antimicrobial and Antiviral Applications:
Due to its inherent antimicrobial and antiviral properties, 4,6-DIIODOPYRIMIDINE is used in the development of agents that can combat various infectious diseases. Its potential to inhibit the growth of harmful microorganisms makes it a promising candidate for use in treatments and preventative measures against infections.

InChI:InChI=1/C4H2I2N2/c5-3-1-4(6)8-2-7-3/h1-2H

Upstream product

• 1193-21-1 4,6-dichloropyrimidine 

Downstream Products

• 161489-05-0 4-Iodo-6-methoxypyrimidine 
• 53557-69-0 6-iodopyrimidin-4-ylamine 
• 141034-81-3 4,6-bis(4-bromophenyl)pyrimidine 
• 609355-99-9 4,6-bis(4-methoxycarbonylphenyl)pyrimidine 
• 934180-28-6 C₆₂H₇₄N₄O₆ 
• 168915-00-2 4,6-bis(4-fluorophenyl)pyrimidine 
• 892413-90-0 N-[(4-chloro-2-[(6-iodo-4-pyrimidinyl)amino]phenyl)acetyl]-L-leucine 1,1-dimethylethyl ester 
• 1018473-92-1 4,6-bis-phenylethynylpyrimidine 
• 1018473-93-2 4,6-bis-4-(N,N-dimethylamino)phenylethynylpyrimidine 
• 1150111-42-4 N-(3-fluorophenyl)-6-iodo-4-pyrimidinamine 
• 1258878-87-3 tert-butyl 4'-(1-(6-iodopyrimidin-4-yl)-8-[[3-methylpyridin-2-yl]methyl]-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)-biphenyl-4-carboxylate 
• 1450722-42-5 4,6-bis-[4-(2,6-diphenyl-pyran-4-ylidenemethyl)-phenylethynyl]-pyrimidine 
• 693793-27-0 C₁₉H₂₆IN₇OSi 

Relevant articles and documents

Synthesis and coordination chemistry of doubly-tridentate tripodal pyridazine and pyrimidine-derived ligands: Structural interplay between M 2L and M2L2 (M = Ni and Pd) complexes and magnetic properties of iron(II) complexes

The coordination chemistry of three bridging doubly-tridentate ligands, including the known compound 3,6-bis(di-2-pyridylmethyl)pyridazine (1), which is structurally similar to 1,4-bis(di-2-pyridylmethyl)phthalazine (2), and two pyrimidine-linked compounds 4,6-bis(di-2-pyridylmethyl)pyrimidine (3), and 4,6-bis(di-2-pyridylamino)pyrimidine (4), was investigated with FeII, NiII, and PdII metal salts. Ligands 3 and 4 were synthesized in one-pot reactions from easily obtained starting materials; compound 3 was synthesized from di-2-pyridylmethane and 4,6-diiodopyrimidine in 48% yield, while ligand 4 was prepared by reacting di-2-pyridylamine with 4,6-dichloropyrimidine in 27% yield. During the synthesis of 4, an additional compound, 4-chloro-6-(di-2-pyridylamino)pyrimidine (5), with only one tridentate binding site was obtained in 30% yield. Reactions of 1, 3, and 4 with Fe II or NiII salts gave two types of complexes, either discrete M2L or M2L2 assemblies. The Pd II complexes obtained were also characterized as discrete M 2L complexes. The compounds were characterized by a combination of NMR and IR spectroscopy, microanalysis and X-ray crystallography. Noticeable differences in the structures obtained for NiII coordination complexes with the carbon-linked (3) and nitrogen-linked (4) ligands were observed, whereby the nitrogen linker adopted a trigonal planar geometry and prevented tridentate facial coordination of the octahedral metal centres. The magnetic properties of dinuclear FeII complexes of 1 were examined to see if they showed spin-crossover effects, a feature recently observed by others in other dinuclear helicate complexes, but the complexes remained high-spin at all temperatures between 300 and 2 K. CSIRO 2009.

Finely Resolved Threshold for the Sharp M12L24/M24L48 Structural Switch in Multi-Component MnL2n Polyhedral Assemblies: X-ray, MS, NMR, and Ultracentrifugation Analyses

In the self-assembly of MnL2n polyhedra, the bend angle (θ) of the divalent ligand components determines the final structure. The threshold for the sharp structural switch between M12L24 and M24L48 was finely resolved to within just 4 by demonstrating the exclusive formation of M12L24 cuboctahedra or M24L48 rhombicuboctahedra from two similar ligands with θ values of 130 and 134. This sharp structural switch was fully confirmed by X-ray crystallography, mass spectrometry, NMR spectroscopy, and ultracentrifugation analyses.

Bis- and tris(arylethynyl)pyrimidine oligomers: synthesis and light-emitting properties

In this contribution, we describe the synthesis of bis- and tris(arylethylnyl)pyrimidine oligomers using Sonogashira, Negishi and Suzuki cross-coupling reactions and starting from chloro or iodopyrimidines. When the arms of such banana-shaped and star-sha

Pyrazolo[1,5-a]pyridine antiherpetics: Effects of the C3 substituent on antiviral activity

A recently disclosed series of pyrazolo[1,5-a]pyridine inhibitors of herpes virus replication has been closely examined herein for effects of the C3 substituent on antiviral activity. Significant changes in activity are observed by alterations of the hete

4-Amino-5-aryl-6-arylethynylpyrimidines: Structure-activity relationships of non-nucleoside adenosine kinase inhibitors

A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT-702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-ylpyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed.

Novel vanilloid receptor-1 antagonists: 3. The identification of a second-generation clinical candidate with improved physicochemical and pharmacokinetic properties

Based on the previously reported clinical candidate, AMG 517 (compound 1), a series of related piperazinylpyrimidine analogues were synthesized and evaluated as antagonists of the vanilloid 1 receptor (VR1 or TRPV1). Optimization of in vitro potency and physicochemical and pharmacokinetic properties led to the discovery of (R)-N-(4-(6-(4-(1-(4-fluorophenyl)ethyl) piperazin-1-yl)pyrimidin-4-yloxy)benzo[d]-thiazol-2-yl)acetamide (16p), a potent TRPV1 antagonist [rTRPV1(CAP) IC50 = 3.7 nM] with excellent aqueous solubility (≥200 μg/mL in 0.01 N HCl) and a reduced half-life (rat t 1/2 = 3.8 h, dog t1/2 = 2.7 h, monkey t1/2 = 3.2 h) as compared to AMG 517. In addition, compound 16p was shown to be efficacious at blocking a TRPV1-mediated physiological response in vivo (ED 50 = 1.9 mg/kg, p.o. in the capsaicin-induced flinch model in rats) and was also effective at reducing thermal hyperalgesia induced by complete Freund's adjuvant in rats (MED = 1 mg/kg, p.o). Based on its improved overall profile, compound 16p (AMG 628) was selected as a second-generation candidate for further evaluation in human clinical trials as a potential new treatment for chronic pain.

Vanilloid receptor ligands and their use in treatments

Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache,

PHENYL OR HETEROARYL AMINO ALKANE DERIVATIVES AS IP RECEPTOR ANTAGONIST

The present invention relates to a phenyl or heteroaryl amino alkane derivatives which are useful as an active ingredient of pharmaceutical preparations. The phenyl or heteroaryl amino alkanes of the present invention have IP receptor antagonistic activity, and can be used for the prophylaxis and treatment of diseases associated with IP receptor antagonistic activity. Such diseases include urological diseases or disorder as follows: bladder outlet obstruction, overactive bladder, urinary incontinence, detrusor hyper-reflexia, detrusor instability, reduced bladder capacity, frequency of micturition, urge incontinence, stress incontinence, bladder hyperreactivity, benighn prostatic hypertrophy (BPH), prostatitis, urinary frequency, nocturia, urinary urgency, pelvic hypersensitivity, urethritis, pelvic pain syndrome, prostatodynia, cystitis, or idiophatic bladder hypersensitivity. The compounds of the present invention are also useful for treatment of pain including, but not limited to inflammatory pain, neuropathic pain, acute pain, chronic pain, dental pain, premenstrual pain, visceral pain, headaches, and the like; hypotension; hemophilia and hemorrhage; and inflammation, since the diseases also is alleviated by treatment with an IP receptor antagonist.

Design, synthesis, and structure-activity relationship of 6-alkynylpyrimidines as potent adenosine kinase inhibitors

Adenosine (ADO) is an extracellular signaling molecule within the central and peripheral nervous system. Its concentration is increased at sites of tissue injury and inflammation. One of the mechanisms by which antinociceptive and antiinflammatory effects of ADO can be enhanced consists of inhibition of adenosine kinase (AK), the primary metabolic enzyme for ADO. Novel nonnucleoside AK inhibitors based on 4-amino-6-alkynylpyrimidines were prepared, and the importance of the length of the linker at the 5-position for high affinity AK inhibition was demonstrated. Compounds with 2- and 3-atom linkers were the most potent AK inhibitors. Optimization of their physicochemical properties led to 31a and 37a that effectively reduced pain and inflammation in animal models.

Desymmetrization of dichloroazaheterocycles

3,6-Dichloropyridizine 1a was converted in good yield into its mono-iodo derivative 1b when treated with a mixture of hydriodic acid and sodium iodide. Pure samples of the mono-iodo derivatives 2b, 3b and 4b could not be obtained from their corresponding dichlorinated precursors with these reagents. Compounds 1b and 4b underwent palladium catalysed Suzuki, Sonogashira and other coupling reactions.