19752-61-5

Basic information

• Product Name: 2,4-DI-(TERT-BUTOXY)-5-BROMOPYRIMIDINE
• Synonyms: IFLAB-BB F1371-0151;5-BROMO-2,4-DI-(TERT-BUTOXY)PYRIMIDINE;2,4-DI-T-BUTOXY-5-BROMO-PYRIMIDINE;2,4-DI-(TERT-BUTOXY)-5-BROMOPYRIMIDINE;5-broMo-2,4-bis(tert-butoxy)pyriMidine;5-BroMo-2,4-bis(1,1-diMethylethoxy)pyriMidine;5-bromo-2,4-bis[(2-methylpropan-2-yl)oxy]pyrimidine
• CAS NO: 19752-61-5
• Molecular Formula: C₁₂H₁₉BrN₂O₂
• Molecular Weight: 303.2
• Product Categories: Pyrimidines
• Mol File: 19752-61-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 58-61°C
• Boiling Point: 352 °C at 760 mmHg
• Flash Point: 166.7 °C
• Appearance: /
• Density: 1.267 g/cm³
• Vapor Pressure: 8.05E-05mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DCM, Ethyl Acetate, Methanol
• PKA: 1.73±0.29(Predicted)
• CAS DataBase Reference: 2,4-DI-(TERT-BUTOXY)-5-BROMOPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DI-(TERT-BUTOXY)-5-BROMOPYRIMIDINE(19752-61-5)
• EPA Substance Registry System: 2,4-DI-(TERT-BUTOXY)-5-BROMOPYRIMIDINE(19752-61-5)

Safety Data

• Hazardous Substances Data: 19752-61-5(Hazardous Substances Data)

Usage

Description

2,4-DI-(TERT-BUTOXY)-5-BROMOPYRIMIDINE, also known as 5-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine, is an organic compound that serves as an intermediate in the synthesis of β-Pseudouridine, a nucleoside isomer of uridine found in various RNA classes across different species.

Uses

Used in Pharmaceutical Industry:
2,4-DI-(TERT-BUTOXY)-5-BROMOPYRIMIDINE is used as a chemical intermediate for the synthesis of β-Pseudouridine (O839607), which is an important component of many classes of RNA, except mRNA. Its role in RNA synthesis and function makes it a valuable compound in the development of pharmaceuticals targeting RNA-related diseases and conditions.

Synthesis

5-Bromo-2,4-dichloropyrimidine (10.0 mmol, 2.28 g) is dissolved in dry THF (50 mL). Then a solution of sodium tert-butoxide (25.0 mmol, 2.40 g) in THF (100 mL) is added dropwise at rt and the reaction mixture stirred for 5 h. The reaction is quenched with water (50 mL) and extracted with EtOAc (3 x 50 mL). Purification by flash chromatography yielded the desired product 5 as colorless solid (2.79 g, 92%). 5-Bromo-2,4-di-tert-butoxypyrimidine 5 ,Yield 2.79 g, 92%.

InChI:InChI=1/C12H19BrN2O2/c1-11(2,3)16-9-8(13)7-14-10(15-9)17-12(4,5)6/h7H,1-6H3

Upstream product

• 36082-50-5 2,4-dichloro-5-bromopyrimidine 
• 865-48-5 sodium t-butanolate 
• 865-47-4 potassium tert-butylate 

Downstream Products

• 28399-56-6 (1R)-D-O²,O⁴;O³,O⁵-(R,R)-dibenzylidene-1-(2,4-di-tert-butoxy-pyrimidin-5-yl)-D-ribitol 
• 28399-56-6 (1S)-O²,O⁴;O³,O⁵-(R,R)-dibenzylidene-1-(2,4-di-tert-butoxy-pyrimidin-5-yl)-D-ribitol 
• 78119-22-9 5-(2,3,5-tri-O-benzyl-D-altro-pentahydroxypentyl)-2,4-di-t-butoxypyrimidine 
• 78119-23-0 5-(2,3,5-tri-O-benzyl-D-allo-pentahydroxypentyl)-2,4-di-t-butoxypyrimidine 
• 172949-72-3 2,4-Di-tert-butoxy-pyrimidine-5-carbaldehyde 
• 28455-50-7 (R)-(2,4-Di-tert-butoxy-pyrimidin-5-yl)-((4S,4aR,8aR)-2,6-diphenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-methanol 
• 28399-56-6 (S)-(2,4-Di-tert-butoxy-pyrimidin-5-yl)-((4S,4aR,8aR)-2,6-diphenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-methanol 
• 910859-94-8 2,4-di-tert-butoxy-5-(3,4,5-trimethoxybenzyl)pyrimidine 
• 28399-65-7 O²,O⁴;O³,O⁵-(R,R)-dibenzylidene-1-(2,4-di-tert-butoxy-pyrimidin-5-yl)-D-ribo-[1]pentulose 
• 109299-79-8 (2,4-di-tert-butoxypyrimidin-5-yl)boronic acid 
• 1381926-43-7 C₃₉H₅₀N₂O₇ 

Relevant articles and documents

Synthesis, characterization, and in vitro evaluation of the selective P2Y2 receptor antagonist AR-C118925

The Gq protein-coupled, ATP- and UTP-activated P2Y2 receptor is a potential drug target for a range of different disorders, including tumor metastasis, inflammation, atherosclerosis, kidney disorders, and osteoporosis, but pharmacological studies are impeded by the limited availability of suitable antagonists. One of the most potent and selective antagonists is the thiouracil derivative AR-C118925. However, this compound was until recently not commercially available and little is known about its properties. We therefore developed an improved procedure for the synthesis of AR-C118925 and two derivatives to allow up-scaling and assessed their potency in calcium mobilization assays on the human and rat P2Y2 receptors recombinantly expressed in 1321N1 astrocytoma cells. The compound was further evaluated for inhibition of P2Y2 receptor-induced β-arrestin translocation. AR-C118925 behaved as a competitive antagonist with pA2 values of 37.2?nM (calcium assay) and 51.3?nM (β-arrestin assay). Selectivity was assessed vs. related receptors including P2X, P2Y, and adenosine receptor subtypes, as well as ectonucleotidases. AR-C118925 showed at least 50-fold selectivity against the other investigated targets, except for the P2X1 and P2X3 receptors which were blocked by AR-C118925 at concentrations of about 1?μM. AR-C118925 is soluble in buffer at pH 7.4 (124?μM) and was found to be metabolically highly stable in human and mouse liver microsomes. In Caco2 cell experiments, the compound displayed moderate permeability indicating that it may show limited peroral bioavailability. AR-C118925 appears to be a useful pharmacological tool for in vitro and in vivo studies.

Synthesis of functionalized diarylmethanes via a copper-catalyzed cross-coupling of arylmagnesium reagents with benzylic phosphates

A combination of copper chloride, triethyl phosphite, and tetrabutylammonium iodide is a very efficient catalytic system for the synthesis of polyfunctionalized diarylmethanes, using the cross-coupling reaction of arylmagnesium halides with benzylic phosphates. The antibiotic Trimethoprim has been prepared using this Cu(I)-catalyzed cross-coupling in 52% overall yield (four steps).

Uracil compounds as P2-purinoreceptor 7-transmembrane G-protein coupled receptor antagonists

Compounds of formula I or salts thereof where for example Y is a group of the formula (i) and R1is a group of formula (ii) are provided along with compositions containing them and processes for their preparation. The compounds are P2-purinoreceptor 7-transmembrane G-protein coupled receptor antagonists, and are useful in the treatment of inflammatory conditions.