953776-62-0

Basic information

• Product Name: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin
• Synonyms: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin;N-[4-(4-Fluorophenyl)-5-Methyl-6-(1-Methylethyl)-2-pyriMidinyl]-N-MethylMethanesulfonaMide
• CAS NO: 953776-62-0
• Molecular Formula: C₁₆H₂₀FN₃O₂S
• Molecular Weight: 337.4123032
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 953776-62-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 118 °C
• Boiling Point: 471.0±47.0 °C(Predicted)
• Appearance: /
• Density: 1.246±0.06 g/cm3(Predicted)
• PKA: 0.43±0.10(Predicted)
• CAS DataBase Reference: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin(953776-62-0)
• EPA Substance Registry System: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin(953776-62-0)

Safety Data

• Hazardous Substances Data: 953776-62-0(Hazardous Substances Data)

Usage

Uses

N-[4-(4-Fluorophenyl)-5-methyl-6-(1-methylethyl)-2-pyrimidinyl]-N-methylmethanesulfonamide is an important pyrimidine precursors for rosuvastatin synthesis.

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 articles and documents

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.

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.

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.