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

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

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

• 147118-36-3 N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 
• 953776-62-0 N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide 
• 147118-30-7 ethyl 2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-carboxylic acid 
• 925422-06-6 N-[5-chloromethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide 
• 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 
• 147118-37-4 N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 956034-83-6 C₂₄H₂₄F₃N₅O₃S₂ 
• 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 
• 289042-10-0 N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide 
• 853066-73-6 tributyl[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-ylmethyl]phosphonium bromide 
• 1210451-23-2 N-{4-(4-fluorophenyl)-6-isopropyl-5-[(pyridin-2-ylthio)methyl]pyrimidin-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 
• 147118-36-3 N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 
• 1234331-53-3 N-{5-[(benzo[d]thiazol-2-ylthio)methyl]-4-(4-fluorophenyl)-6-isopropylpyrimidin-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 
• 956034-92-7 N-{4-(4-fluorophenyl)-6-isopropyl-5-[(1-methyl-1H-benzo[d]imidazol-2-ylsulfonyl)methyl]pyrimidin-2-yl}-N-methylmethanesulfonamide 
• 1221497-92-2 dimethyl [4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino]pyrimidine-5-ylmethyl]phosphonate 
• 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 

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%.

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.

A novel process for synthesis of Rosuvastatin

A novel process for the preparation of antihypercholesterolemic drug rosuvastatin calcium using novel intermediates has been described. Novel intermediates have been characterized by using IR, NMR and Mass spectroscopy.

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.

KEY INTERMEDIATES FOR THE SYNTHESIS OF ROSUVASTATIN OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The present invention relates in general to the field of organic chemistry and in particular to the preparation of N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide (I), N-(4-(4-fluorophenyl)-5-(bromomethyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (II) and N-(4-(4-fluorophenyl)-5-(hydroxymethyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (III), key intermediates in preparation of Rosuvastatin.

PROCESS FOR THE PREPARATION OF HMG-COA REDUCTASE INHIBITORS AND INTERMEDIATES THEREOF

The present invention provides an improved process for preparing HMG-CoA reductase inhibitors such as rosuvasatin calcium, fluvastatin sodium, and pitavastatin calcium under a mild condition, using a novel amide-bond-containing compound having R2-N-O-R1 moiety as a key intermediate. And also, the present invention provides the novel compound, an intermediate useful for the preparation thereof, and a process for the preparation thereof.

PROCESS FOR THE PREPARATION OF KEY INTERMEDIATES FOR THE SYNTHESIS OF STATINS OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The invention relates to commercially viable process for the synthesis of key intermediates for the preparation of statins, in particular Rosuvastatin and Pitavastatin or respective pharmaceutically acceptable salts thereof. A new simple and short synthetic route for key intermediates is presented which benefits from the use of cheap and readily available starting materials, by which the conventionally most frequently used DIBAL-H as reducing agent can be avoided.

Concise and highly efficient approach to three key pyrimidine precursors for rosuvastatin synthesis

We report the synthesis of 5-formyl-, 5-(hydroxymethyl)-, and 5-(bromomethyl) substituted N-[4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N- methylmethanesulfonamide. The presented synthetic approach is based on highly efficient three step preparation of functionalized 5-methylpyrimidine. The methyl group is selectively brominated by NBS with irradiation into the bromomethyl derivative, which is then transformed into the hydroxymethyl or formyl groups in nearly quantitative yields. This approach is superior to the existing methodologies for the preparation of the key pyrimidine precursors used in the synthesis of rosuvastatin since no metal catalysis and no cryogenic reaction conditions are involved.

Process for the preparation of key intermediates for the synthesis of statins or pharmaceutically acceptable salts thereof

The invention relates to commercially viable process for the synthesis of key intermediates for the preparation of statins, in particular Rosuvastatin and Pitavastatin or respective pharmaceutically acceptable salts thereof. A new simple and short synthetic route for key intermediates is presented which benefits from the use of cheap and readily available starting materials, by which the conventionally most frequently used DIBAL-H as reducing agent can be avoided.