Ethyl 4-(4-Fluorophenyl)-6-isopropyl-2-methylthiopyrimidine-5-carboxylate

Base Information

• Chemical Name: Ethyl 4-(4-Fluorophenyl)-6-isopropyl-2-methylthiopyrimidine-5-carboxylate
• CAS No.: 147118-27-2
• Molecular Formula: C17H19FN2O2S
• Molecular Weight: 334.414
• Mol file: 147118-27-2.mol

Synonyms:Ethyl 4-(4-Fluorophenyl)-6-isopropyl-2-methylthiopyrimidine-5-carboxylate

Chemical Property of Ethyl 4-(4-Fluorophenyl)-6-isopropyl-2-methylthiopyrimidine-5-carboxylate

Chemical Property:

• Boiling Point: 483.6±45.0 °C(Predicted)
• PKA: -0.44±0.50(Predicted)
• PSA: 77.38000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 4.30470
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

Ethyl4-(4-Fluorophenyl)-6-isopropyl-2-methylthiopyrimidine-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate of Rosuvastatin (R700500).

Technology Process of Ethyl 4-(4-Fluorophenyl)-6-isopropyl-2-methylthiopyrimidine-5-carboxylate

There total 8 articles about Ethyl 4-(4-Fluorophenyl)-6-isopropyl-2-methylthiopyrimidine-5-carboxylate 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: 97.0%

ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-1,4-dihydropyrimidine-5-carboxylate (1619238-14-0) → ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-pyrimidine-5-carboxylate (147118-27-2)

Guidance literature:

With potassium carbonate; eosin Y bis(tetrabutyl ammonium salt); In methanol; water; at 20 ℃; chemoselective reaction; Irradiation;

DOI:10.1039/c4gc00337c

Reference yield: 68.0%

5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylthio)-1,4-dihydropyrimidine + tert.-butylhydroperoxide (75-91-2) → ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)pyrimidine-5-carboxylate + 5-(tert-butylperoxy)-5-ethoxycarbonyl-6-(4-fluorophenyl)-4-isopropyl-2-(methylthio)-4,5-dihydropyrimidine + ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-pyrimidine-5-carboxylate (147118-27-2)

Guidance literature:

With potassium carbonate; copper dichloride; In dichloromethane; water; at 38 - 40 ℃; for 24h;

DOI:10.1021/ol051879w

Reference yield:

ethyl 4-methyl-3-oxo-pentanoate (7152-15-0) → ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-pyrimidine-5-carboxylate (147118-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86.7 percent / piperidine, AcOH / benzene / Heating

2: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min

With piperidine; N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene;

DOI:10.1016/S0968-0896(96)00248-9

upstream raw materials:

S-Methylisothiourea sulfate

(E)-2-<(4-fluorophenyl)methylene>-4-methyl-3-oxopentanoic acid ethyl ester

tert.-butylhydroperoxide

4-fluorobenzaldehyde

Downstream raw materials:

7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonamido)-pyrimidin-5-yl)-(3R)-3-tert-butyldimethylsiloxy-5-oxo-(E)-6-heptenoic acid methyl ester

(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid methyl ester

methyl (3R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate