41244-53-5

Basic information

• Product Name: 2 , 4-BIS(BENZYLOXY)-5-BROMOPYRIMIDINE
• Synonyms: 5-bromo-2,4-bis(phenylmethoxy)- Pyrimidine
• CAS NO: 41244-53-5
• Molecular Formula: C₁₈H₁₅BrN₂O₂
• Molecular Weight: 371.233
• Product Categories: Pyrimidines;Heterocycle-Pyrimidine series
• Mol File: 41244-53-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 517.4 °C at 760 mmHg
• Flash Point: 266.7 °C
• Appearance: /
• Density: 1.419 g/cm³
• Vapor Pressure: 2.7E-10mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2 , 4-BIS(BENZYLOXY)-5-BROMOPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2 , 4-BIS(BENZYLOXY)-5-BROMOPYRIMIDINE(41244-53-5)
• EPA Substance Registry System: 2 , 4-BIS(BENZYLOXY)-5-BROMOPYRIMIDINE(41244-53-5)

Safety Data

• Hazardous Substances Data: 41244-53-5(Hazardous Substances Data)

Usage

Description

2,4-Bis(benzyloxy)-5-bromopyrimidine is a chemical compound that belongs to the pyrimidine family. It is characterized by its molecular formula C17H15BrN2O2 and a molecular weight of 374.22 g/mol. 2 , 4-BIS(BENZYLOXY)-5-BROMOPYRIMIDINE is recognized for its role in organic synthesis and pharmaceutical research, where it serves as a building block for the synthesis of various biologically active molecules.

Uses

Used in Pharmaceutical Research and Development:
2,4-Bis(benzyloxy)-5-bromopyrimidine is used as a key intermediate in the production of pharmaceutical drugs. Its unique structure and properties make it a valuable component in the development of new medicines, contributing to the advancement of treatments for a range of diseases and disorders.
Used in Organic Synthesis:
In the field of organic synthesis, 2,4-Bis(benzyloxy)-5-bromopyrimidine is utilized as a versatile building block. Its reactivity and functional groups allow for the creation of a variety of complex organic molecules, which can be further used in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
2,4-Bis(benzyloxy)-5-bromopyrimidine has potential applications in medicinal chemistry, where it can be employed in the design and synthesis of novel therapeutic agents. Its presence in the pyrimidine family suggests that it may have biological activity, making it a promising candidate for the treatment of various diseases and disorders.

InChI:InChI=1/C18H15BrN2O2/c19-16-11-20-18(23-13-15-9-5-2-6-10-15)21-17(16)22-12-14-7-3-1-4-8-14/h1-11H,12-13H2

Upstream product

• 36082-50-5 2,4-dichloro-5-bromopyrimidine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 67320-14-3 (1Ξ)-O²,O⁴;O³,O⁵-(R,R)-dibenzylidene-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-D-ribitol 
• 13039-96-8 (1R)-1-(2,4-bis-benzyloxy-pyrimidin-5-yl)-O²,O³;O⁴,O⁵-diisopropylidene-D-xylitol 
• 109299-83-4 4-bis(benzyloxy)-5-(thiophen-2-yl)pyrimidine 
• 325771-87-7 2,4-bis-benzyloxy-5-iodo-pyrimidine 
• 1355048-90-6 C₃₀H₂₅N₂O₂P 
• 120825-37-8 2,4-dibenzyloxy-5-trimethylstannylpyrimidine 
• 62803-28-5 2,4-dibenzyloxy-5-trimethylsilylpyrimidine 
• 848945-14-2 2,4-Bis-benzyloxy-5-[1-((2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-imidazol-4-yl]-pyrimidine 
• 70523-24-9 5-(dihydroxyboryl)-2,4-bis(benzyloxy)pyrimidine 
• 28485-24-7 1,5-dibenzylpyrimidine-2,4(1H,3H)-dione 
• 128376-62-5 2,4-dibenzyloxy-5-lithiopyrimidine 

Relevant articles and documents

Synthesis of 5-(Dihydroxyboryl)-2'-deoxyuridine and Related Boron-Containing Pyrimidines

Organoboron derivatives of pyrimidines and of 2'-deoxyribonucleosides have been synthesized as potential antiviral and anticancer agents.The first 5-boron-substituted pyrimidine nucleoside, 5-(dihydroxyboryl)-2'-deoxyuridine, has been prepared via a metal-halogen exchange at -50 deg C in tetrahydrofuran on 5-bromo-3',5'-bis (O-trimethylsilyl)-2'-deoxyuridine using n-butyllithium followed by boronation at -65 deg C with tri-n-butyl borate in the presence of HMPT.After hydrolysis, the product was purified by column chromatography and repeated fractional crystallization and the purity determined by HPLC.This hydrolytically stable compound showed no activity against Sarcoma 180 (S-180) but inhibited herpes simplex virus type 1 at a nontoxic concentration.The compound sensitized hamster V-79 cells to neutrons and could be of potential use in boron neutron capture therapy. 5-(Dihydroxyboryl)uracil and 6-(dihydroxyboryl)uracil were prepared also by a similar route from the corresponding 5- or 6-bromo-2,4-bis(benzyloxy)pyrimidine.However, the mixture was maintained at -85 deg C during the whole reaction sequence and the product was obtained by hydrolysis followed by catalytic hydrogenation.The physical characteristics of these analogues, as well as those of their iminodiethanol esters, are described.

Synthesis and coordination chemistry of pyrimidine-substituted phosphine ligands

Reaction of PPh2H with UrI (Ur = uracil) in the presence of Pd(OAc)2 affords PPh2Ur. In the solid state, PPh 2Ur crystallises as a methanol solvate in the monoclinic space group P21/c. Reaction of PPh2Ur with CuI in dry and deoxygenated THF solution results in the formation of [Cu4(μ3-I) 4(PPh2Ur)4]. A single crystal X-ray diffraction study demonstrated that this species contains a distorted tetrahedral core of copper atoms, with facially-capping iodides. The uracil groups in the clusters are engaged in hydrogen bonding to groups on neighbouring molecules to form an extended array. A similar reaction between PPh2Ur and CuI in unpurified THF allows for the isolation of the phosphine oxide P(O)PPh 2Ur. The synthesis of the benzyl-protected phosphine PPh 2UrP is also described [UrP = 2,4-bis(benzyloxy)pyrimidine]. Reaction of PPh2UrP with [Ru(η5-C5H5)(NCMe)3]PF 6 allows for isolation of [Ru(η5-C5H 5)(NCMe)(PPh2UrP)2]PF6.

"Molecular chameleons". Design and synthesis of a second series of flexible nucleosides

(Chemical Equation Presented) The second series of flexible shape-modified nucleosides is introduced. The "fleximers" feature the purine ring systems split into their individual imidazole and pyrimidine components. This structural modification serves to introduce flexibility to the nucleoside while still retaining the elements essential for recognition. As a consequence, these structurally innovative nucleosides can more readily adapt to their environment and should find use as bioprobes for investigating enzyme-coenzyme binding sites as well as nucleic acid and protein interactions. Their design and synthesis is described.