953776-62-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin is used as a key intermediate in the synthesis of Rosuvastatin, a cholesterol-lowering drug. It plays a crucial role in the production of this medication, which helps in reducing the levels of low-density lipoprotein (LDL) cholesterol and triglycerides in the blood, thereby lowering the risk of cardiovascular diseases.
Used in Drug Development:
5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin can be used as a starting material for the development of new drugs with improved pharmacological properties. Its unique chemical structure allows for further modifications and optimization, potentially leading to the discovery of novel therapeutic agents with enhanced efficacy and safety profiles.
Used in Research and Development:
5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin can be employed as a research tool in the study of cholesterol metabolism and the development of new treatments for hypercholesterolemia and related conditions. Its unique structure and properties make it a valuable compound for investigating the mechanisms of action and potential applications of Rosuvastatin and its analogs.
Used in Chemical Synthesis:
5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin can be utilized in various chemical synthesis processes, such as the preparation of other pyrimidine derivatives or the development of new chemical compounds with potential applications in different industries, including pharmaceuticals, agrochemicals, and materials science.

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 
• 124-63-0 methanesulfonyl chloride 
• 1246665-81-5 C₂₈H₄₅FN₃O₂PS 
• 1068433-24-8 (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 799842-07-2 N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 
• 147118-37-4 N-[4-(4-fluorophenyl)-5-formyl-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 
• 1416000-58-2 N-(4-(2-bromopropan-2-yl)-6-(4-fluorophenyl)-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide 
• 1416000-55-9 N-(5-(bromomethyl)-4-(2-bromopropan-2-yl)-6-(4-fluorophenyl)pyrimidin-2-yl)-N-methylmethanesulfonamide 
• 1416000-51-5 N-(5-(dibromomethyl)-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 

Relevant academic research and scientific papers

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 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.

Lactone pathway to statins utilizing the wittig reaction. the synthesis of rosuvastatin

The first entry to statins via lactonized side chain is reported, exemplified by the synthesis of rosuvastatin. The key step is Wittig coupling of (2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-carbaldehyde and phosphonium salt of an appropriately functionalized pyrimidine heterocy'le. One-pot deprotection and hydrolysis of the resulting 4-O-TBS rosuvastatin lactone provided rosuvastatin in high yield.

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.