52522-99-3

Basic information

• Product Name: 5-Iodo-2,4-dimethoxypyrimidine
• Synonyms: 5-IODO-2,4-DIMETHOXYPYRIMIDINE;2,4-Dimethoxy-5-iodopyrimidine;3-METHYLPHTHALIC ACID;5-Iodo-2,4-dimethoxypyrimidine ,98%;2,3-Toluenedicarboxylic acid;3-Methylbenzene-1,2-dicarboxylic acid
• CAS NO: 52522-99-3
• Molecular Formula: C₆H₇IN₂O₂
• Molecular Weight: 266.04
• Product Categories: Pyrimidine;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Nucleoside AnalogsHeterocyclic Building Blocks;Biochemicals and Reagents;Nucleosides, Nucleotides, Oligonucleotides;Nucleoside Analogs;Biochemicals and Reagents;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Nucleosides;Nucleotides;Oligonucleotides;C6 to C8;Heterocycle-Pyrimidine series
• Mol File: 52522-99-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 71-75 °C(lit.)
• Boiling Point: 328.7 °C at 760 mmHg
• Flash Point: 152.6 °C
• Appearance: /
• Density: 1.822 g/cm³
• Vapor Pressure: 2.55E-06mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: −20°C
• Solubility: Chloroform; Dichloromethane
• PKA: 1.33±0.29(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 5-Iodo-2,4-dimethoxypyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Iodo-2,4-dimethoxypyrimidine(52522-99-3)
• EPA Substance Registry System: 5-Iodo-2,4-dimethoxypyrimidine(52522-99-3)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• HazardClass: IRRITANT, TOXIC
• Hazardous Substances Data: 52522-99-3(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Synthesis Reference(s)

Different sources of media describe the Synthesis Reference(s) of 52522-99-3 differently. You can refer to the following data:
1. Journal of the American Chemical Society, 82, p. 4753, 1960 DOI: 10.1021/ja01502a085
2. Synthetic Communications, 18, p. 855, 1988 DOI: 10.1080/00397918808057855

InChI:InChI=1/C9H8O4/c1-5-3-2-4-6(8(10)11)7(5)9(12)13/h2-4H,1H3,(H,10,11)(H,12,13)

Upstream product

• 3551-55-1 2,4-dimethoxypyrimidine 
• 18677-43-5 2,4-dimethoxypyridine 
• 124-41-4 sodium methylate 
• 13544-44-0 2,4-dichloro-5-iodopyrimidine 
• 67-56-1 methanol 
• 696-07-1 5-iodouracil 
• 123551-51-9 5,5'-Mercuri-bis-(2,4-dimethoxypyrimidine) 
• 123551-48-4 5-Acetoxymercuri-2,4-dimethoxypyrimidine 

Downstream Products

• 267890-23-3 2-{N-Benzyl-N-[3'-(2,4-dimethoxypyrimidin-5-yl)prop-2'-ynyl]amino}benzoic acid 
• 260803-80-3 3-(2-aminophenylthio)-1-(2,4-dimethoxypyrimidin-5-yl)prop-1-yne 
• 935265-59-1 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(2,4-dimethoxypyrimidin-5-yl)oxazole 
• 115492-15-4 2,4-dimethoxy-5-<2-(p-methoxybenzoyl)ethynyl>pyrimidine 
• 115492-11-0 5-(2-benzoylethynyl)-2,4-dimethoxypyrimidine 
• 1379771-58-0 2-((2,4-dimethoxypyrimidin-5-yl)methyl)-1-(toluene-4-sulfonyl)-1H-indole 
• 173436-68-5 2-methyl-1-[(4-methylphenyl)sulfonyl]-1H-indole 
• 1379771-40-0 (E)-2-((2,4-dimethoxypyrimidin-5-yl)methylidene)-1-(toluene-4-sulfonyl)indolin-3-ol 
• 1350705-14-4 2-amino-N-methyl-N-[3-[(2,4-dimethoxy)pyrimidine-5-yl]prop-2-ynyl]benzamide 
• 1232133-37-7 (E)-3-[(2,4-dimethoxypyrimidin-5-yl)methylidene]-4-tosyl-3,4-dihydro-2H-1,4-benzoxazine 
• 1101167-59-2 4-(2,4-dimethoxypyrimidin-5-yl)benzonitrile 
• 122353-03-1 1-(3,4-Dimethoxy-phenyl)-3-(2,4-dimethoxy-pyrimidin-5-yl)-propynone 
• 122352-99-2 1-(3,4-Dimethoxy-phenyl)-3-(2,4-dimethoxy-pyrimidin-5-yl)-prop-2-yn-1-ol 
• 122352-98-1 5-<3-hydroxy-3-(p-methoxyphenyl)prop-1-ynyl>-2,4-dimethoxypyrimidine 

Relevant articles and documents

A general synthetic method of 5-carboranyluracil nucleosides with potential antiviral activity and use in neutron capture therapy

Previous biochemical and pharmacological studies indicated that 5-o- carboranyl-2'-deoxyuridine is a lead candidate for boron neutron capture therapy. This prompted the development of a rapid and stereoselective N1- glycosylation reaction of silylated 5-o-carboranyluracil with a variety of protected sugars. The key intermediate, 5-o-carboranyluracil (6), was prepared from 5-iodouracil in six steps. A novel coupling procedure of the 2,4-dimethoxy-5-ethynylpyrimidine (4) with decaborane without activator was used. Silylated 6 was coupled with a variety of carbohydrates under mild conditions to produce several carborane containing nucleosides. In each case, the stereochemistry and stereoselectivity of the glycosylation reaction was not affected by the presence of the carborane at the 5-position of the uracil and produced exclusively closo [closo-1,2-C2B10H12 cage] nucleosides. This was confirmed by X-ray structure determination of racemic 5-carboranyl- 2',3'-dideoxy-3'-thiauridine. This compound demonstrated an anti-conformation with the oxathiolane ring in a pseudo C-2'-endo conformation. The toxicity profile of the new compounds and their precursors was determined in three cell culture systems, two of human origin (PBM and CEM cells) and one of monkey origin (Vero cells). The compounds were also evaluated for their potential antiviral activity against human immunodeficiency virus and herpes simplex virus in vitro. 5-o-Carboranyl-xylofuranosyluracil (12) demonstrated low toxicity in culture and in mice.

Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species

In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.

Palladium-catalysed heteroannulation with terminal alkynes: A highly regio- and stereoselective synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1- ones

A highly regio- and stereoselective method for the synthesis of (Z)-3- aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)2PdCl2, CuI, and Et3N in DMF mostly at 80°C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd.