P-[[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]methyl]phosphonic acid dimethyl ester

Base Information

• Chemical Name: P-[[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]methyl]phosphonic acid dimethyl ester
• CAS No.: 1221497-92-2
• Molecular Formula: C18H25FN3O5PS
• Molecular Weight: 445.452
• Mol file: 1221497-92-2.mol

Synonyms:Rosuvastatin Intermediates

Chemical Property of P-[[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]methyl]phosphonic acid dimethyl ester

Chemical Property:

• Appearance/Colour: white or almost white power
• PSA: 116.88000
• Density: 1.307
• LogP: 4.86860

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of P-[[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]methyl]phosphonic acid dimethyl ester

There total 2 articles about P-[[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]methyl]phosphonic acid dimethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (799842-07-2) + phosphorous acid trimethyl ester (121-45-9) → dimethyl [4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino]pyrimidine-5-ylmethyl]phosphonate (1221497-92-2)

Guidance literature:

In toluene; at 20 ℃; for 18h; Inert atmosphere; Reflux;

Reference yield:

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (147118-36-3) → dimethyl [4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino]pyrimidine-5-ylmethyl]phosphonate (1221497-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphorus tribromide / toluene; acetonitrile / 1 h / 10 - 20 °C / Inert atmosphere

2: toluene / 18 h / 20 °C / Inert atmosphere; Reflux

With phosphorus tribromide; In toluene; acetonitrile;

Reference yield: 95.0%

dimethyl [4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino]pyrimidine-5-ylmethyl]phosphonate (1221497-92-2) + tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (124752-23-4) → 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 (289042-12-2,1378943-63-5)

Guidance literature:

dimethyl [4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino]pyrimidine-5-ylmethyl]phosphonate; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate; In tetrahydrofuran; at -35 - 0 ℃; for 21h; Product distribution / selectivity;

upstream raw materials:

N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

phosphorous acid trimethyl ester

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Downstream raw materials:

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

Refernces