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

• 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 
• 1207460-34-1 4-(4-fluorophenyl)-6-isopropyl-N,5-dimethylpyrimidin-2-amine 
• 114433-94-2 1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione 
• 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

• 956034-87-0 C₂₄H₂₆FN₅O₃S₂ 
• 956034-90-5 N-((5-(1H-benzo[d]imidazol-2-ylthio)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methyimethanesulfonamide 
• 147118-36-3 N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 
• 1221497-92-2 dimethyl [4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino]pyrimidine-5-ylmethyl]phosphonate 
• 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 
• 1378943-63-5 C₂₉H₄₀FN₃O₆S 
• 851440-21-6 (3R,5S,E)-isopropyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate 
• 937639-31-1 C₂₀H₂₉FN₃O₅PS 

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.

Method for synthesizing rosuvastatin calcium intermediate impurity

The invention discloses a method for synthesizing a rosuvastatin calcium intermediate impurity. The method comprises the following steps: preparing 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl) amino] pyrimidine-5-methanol (3) from 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl) amino] pyrimidine-5-methyl carboxylate (2) through reduction; preparing 5-(bromine methyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino] pyrimidine (4) from the compound (3) through bromination; coupling the compound (4) with the 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl) amino] pyrimidine-5-methanol (3) to generate N,N'-(5,5'-(oxo-di(methylene)) bi(4-(4-fluorophenyl)-6-isopropyl pyrimidine-5,2-di-yl)) bi(N-methyl methanesulfonamide) (1), so as toobtain the rosuvastatin calcium intermediate impurity with high impurity. The synthesized rosuvastatin calcium intermediate impurity can be used as an impurity standard substance in rosuvastatin calcium raw material detection and analysis, and accurate positioning and qualification of impurities in rosuvastatin calcium raw material detection and analysis can be improved; the method disclosed by the invention is cheap and easy in raw material obtaining and simple in operation, the product yield is 65+/-5%, and the HPLC (High Performance Liquid Chromatography) purity is greater than or equal to99%.

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.