799842-07-2

Basic information

• Product Name: 5-(Bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine
• Synonyms: Diphenyl[4-(4-fluorophenyl)-6-isopropyl-2-(N-Methyl-N-MethylsulfonylaMino)PyriMidine PRODUCT:CheMical naMe:Diphenyl[4-(4-fluorophenyl)-6-isopropyl-2-(N-Methyl-N-MethylsulfonylaMino)PyriMidine;5-(BROMOMETHYL)-4(FLUOROPHENYL)6-ISOPROPYL-2METHYL(METHYLSULFONYL ) AMINOPYRIMIDINE;N-[5-Bromomethyl-4-(4-fluorophenyl)-6-isopropropyl-pyrimidine-2-yl]-N-methylmethane sulfonamide;MethanesulfonaMide, N-[5-(broMoMethyl)-4-(4-fluorophenyl)-6-(1-Methylethyl)-2-pyriMidinyl]-N-Methyl-;Rosuvastatin Bromomethyl Impurity;rosuvastatin intermediates Z-8;N-[5-Bromomethyl-4-(4-fluorophenyl)-6-isopropropyl-pyrimidine-2-yl]-N-methylmethane sulfonamid;N-[5-bromomethyl-4-(4-fluorophenyl)-6-(1-methylethyl)-2-pyrimidinyl]-N-methyl-methanesulfonamide
• CAS NO: 799842-07-2
• Molecular Formula: C₁₆H₁₉BrFN₃O₂S
• Molecular Weight: 416.31
• EINECS: 1592732-453-0
• Product Categories: pyrimidine;Fluorine series;rosuvastatin intermediates
• Mol File: 799842-07-2.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 531.178 °C at 760 mmHg
• Flash Point: 275.047 °C
• Appearance: /
• Density: 1.466
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.77±0.10(Predicted)
• CAS DataBase Reference: 5-(Bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(Bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine(799842-07-2)
• EPA Substance Registry System: 5-(Bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine(799842-07-2)

Safety Data

• Hazardous Substances Data: 799842-07-2(Hazardous Substances Data)

Usage

Uses

5-(Bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine is an impurity of Rosuvastatin (R700500), which is a selective, competitive HMG-CoA reductase inhibitor.

InChI:InChI=1/C16H19BrFN3O2S/c1-10(2)14-13(9-17)15(11-5-7-12(18)8-6-11)20-16(19-14)21(3)24(4,22)23/h5-8,10H,9H2,1-4H3

Upstream product

• 114433-94-2 1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione 
• 1207460-34-1 4-(4-fluorophenyl)-6-isopropyl-N,5-dimethylpyrimidin-2-amine 
• 1354455-77-8 1-(4-fluorophenyl)-2-methyl-3-isopropylpropan-1,3-dione 
• 459-57-4 4-fluorobenzaldehyde 
• 147118-37-4 N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide 
• 925422-06-6 N-[5-chloromethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide 
• 147118-30-7 ethyl 2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-carboxylic acid 
• 953776-62-0 N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide 
• 147118-36-3 N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 

Downstream Products

• 289042-10-0 N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide 
• 147118-36-3 N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 
• 853066-73-6 tributyl[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-ylmethyl]phosphonium bromide 
• 503610-43-3 Rosuvastatin lactone 
• 1353637-13-4 E-(6-{2-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide 
• 1353637-14-5 E-(7-{2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl}-[(3R,5S)-3,5-dihydroxy-hept-6-enoic acid])-N-methoxy-N-methyl-amide 
• 147118-37-4 N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide 
• 851440-21-6 (3R,5S,E)-isopropyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate 
• 956034-92-7 N-{4-(4-fluorophenyl)-6-isopropyl-5-[(1-methyl-1H-benzo[d]imidazol-2-ylsulfonyl)methyl]pyrimidin-2-yl}-N-methylmethanesulfonamide 
• 289042-12-2 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester 
• 956034-90-5 N-((5-(1H-benzo[d]imidazol-2-ylthio)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methyimethanesulfonamide 
• 1234331-53-3 N-{5-[(benzo[d]thiazol-2-ylthio)methyl]-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl}-N-methylmethanesulfonamide 
• 1210451-25-4 N-[5-(3,5-bis-trifluoromethyl-phenylsulfanyl methyI)-4-(4-fluoro-phenyl)-6-isopropyI-pyrimidin-2-yl]-N-methyI-methanesulfonamide 
• 1210451-23-2 N-{4-(4-fluorophenyl)-6-isopropyl-5-[(pyridin-2-ylthio)methyl]pyrimidin-2-yl}-N-methylmethanesulfonamide 

Relevant articles and documents

An efficient, cyanide free total synthesis of rosuvastatin calcium

A simple, efficient, cyanide-free protocol for the total synthesis of rosuvastatin calcium was developed from inexpensive, commercially available D-arabinose; the key steps employed were Wittig reaction followed by oxa-Michael addition. The developed synthetic protocol could be adopted for industrial production of rosuvastatin calcium.

Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin

A diastereoselective palladium-catalyzed cyclization of allenyl hemiacetals is described. It permits the selective synthesis of 1,3-dioxane derivatives, precursors for syn-configured 1,3-diols which make an appearance in all of the statin representatives. The reaction allows the total synthesis of Rosuvastatin and Pitavastatin in a straightforward fashion.

Application of flow photochemical bromination in the synthesis of a 5-bromomethylpyrimidine precursor of rosuvastatin: Improvement of productivity and product purity

In this report we present a flow photochemical bromination of a 5-methyl-substituted pyrimidine precursor of rosuvastatin. The study demonstrated that the reaction productivity can be increased markedly with a flow-mode approach compared to a batch-mode synthesis. Indeed, reaction times can be significantly shortened from a range of hours to a range of minutes. Moreover, in addition to process intensification, the study demonstrated that significantly lower overall levels of side products are obtained when photochemical bromination is conducted in a flow mode.