52522-99-3

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

Downstream Products

• 115492-11-0 5-(2-benzoylethynyl)-2,4-dimethoxypyrimidine 
• 122352-96-9 5-(3-hydroxy-3-phenylprop-1-ynyl)-2,4-dimethoxypyrimidine 
• 115492-15-4 2,4-dimethoxy-5-<2-(p-methoxybenzoyl)ethynyl>pyrimidine 
• 80504-47-8 1,2-dihydro-5-iodo-4-methoxy-2-oxo-1-(2'-benzoyloxyethoxymethyl)pyrimidine 
• 130749-67-6 (E)-3-(2,4-Dimethoxy-pyrimidin-5-yl)-1-p-tolyl-propenone 
• 130767-31-6 (E)-3-(2,4-Dimethoxy-pyrimidin-5-yl)-1-(4-methoxy-phenyl)-propenone 
• 122352-97-0 5-<3-hydroxy-3-(p-tolyl)prop-1-ynyl>-2,4-dimethoxypyrimidine 
• 122352-98-1 5-<3-hydroxy-3-(p-methoxyphenyl)prop-1-ynyl>-2,4-dimethoxypyrimidine 
• 152452-80-7 -2,4-dimethoxy-5-(2-m-toluoylvinyl)pyrimidine 
• 148441-00-3 2,4-dimethoxy-(2'S)-5-<2',3'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine 
• 148440-99-7 2,4-dimethoxy-(2'S)-trans-5-<2',5'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine 
• 148441-01-4 2,4-dimethoxy-(2'R)-5-<2',3'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine 
• 148553-57-5 2,4-dimethoxy-(2'R)-trans-5-<2',5'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine 
• 696-07-1 5-iodouracil 

Relevant academic research and scientific papers

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.

Preparation method of magnesium dichloride (2,2,6,6-tetramethylpiperidinde) lithium salt

The invention discloses a preparation method of magnesium dichloride (2,2,6,6-tetramethylpiperididne) lithium salt, and belongs to the technical field of organic synthesis. Under the protection of inert gas, a lithium sheet and 2,2,6,6-tetramethylpiperidi

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.

Nucleic acid derivatives

A compound which comprises a backbone having a plurality of chiral carbon atoms, the backbone bearing a plurality of ligands each being individually bound to a chiral carbon atom of the plurality of chiral carbon atoms, the ligands including one or more pair(s) of adjacent ligands each containing a moiety selected from the group consisting of a naturally occurring nucleobase and a nucleobase binding group, wherein moieties of the one or more pair(s) are directly linked to one another via a linker chain; building blocks for synthesizing the compound; and rises of the compound, particularly in antisense therapy.

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.

Uracil reductase inactivators

The present invention relates to a group of 5-substituted uracil derivatives which are inactivators of uracil reductase and which are particularily useful in cancer chemotherapy, especially in combination with antimetabolite antineoplastic agents such as 5-fluorouracil (5-FU).

Treatment of urogenital cancer with boron neutron capture therapy

Methods and compositions for treating urogenital tumors, and particular, cancer of the prostate, bladder, and kidney, with BCNT, are disclosed. Any boron-containing compound that is sufficiently lipophilic to pass through the appropriate urogenital membranes in a quantity high enough to achieve therapy on irradiation with low-energy neutrons can be used. Carboranyl-containing nucleosides and oligonucleotides are particularly suited for use in BNCT of urogenital tumors. Preferred compounds include 5-carboranyl-2'-deoxyuridine (CDU) and 5-o-carboranyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil (CFAU). Nucleosides and oligonucleotides bearing an -O-[(carboran-1-yl)alkyl]phosphate, S-[(carboran-1-yl)alkyl]phosphorothioate, or Se-[(carboran-1-yl)alkyl]phosphoroselenoate in place of the (carboran-1-yl)phosphonate moiety can be used. Oligonucleotides of specific gene sequences that include one or more 3',5'-linking-(carboran-1-yl)phosphonate moieties can also be used in antisense therapy in the selective modification of gene expression. Compounds can be used in urogenital BNCT therapy that contain boron clusters as a means to enhance lipophilicity wherein the boron is not enriched in 10 B, but instead, in the 11 B isotope. The therapy is accomplished by administering the boron-containing compound by any appropriate route, including by intravenous injection, oral delivery or by catheter or other direct means, in such a manner that the compound accumulates in the target tumor. After desired accumulation of the compound in the tumor, the site is irradiated with an effective amount of low energy neutrons.

Pharmaceutical compositions of 5-substituted uracil compounds

Pharmaceutical compositions containing 5-substituted uracil compounds are disclosed. The compositions are preferably in the form of a tablet or capsule.

NOVEL SYNTHESIS OF 5-HALOURACILS FROM 5-MERCURI-2,4-DIMETHOXYPYRIMIDINES

Direct C-mercuration of 2,4-dimethoxypyrimidine with mercury (II) acetate has been shown to give the 5-mercuri-derivative, which is readily converted, either directly or via 5,5'-mercuribis (2,4-dimethoxypyrimidine), into the 5-halo derivatives.Hydrolysis of the latter with hydrochloric acid affords the 5-halouracils.

AN EFFICIENT METHOD FOR THE IODINATION OF C5-POSITION OF DIALKOXY PYRIMIDINES AND URACIL BASES

N-Iodosuccinimide in trifluoroacetic acid and trifluoroacetic anhydride was found to be an excellent reagent for the conversion of 2,4-dialkoxy pyrimidines to 2,4-dialkoxy-5-iodopyrimidines.Iodination at C5-position of uracil and its derivatives was also accomplished with the above reagent.