N-[5-(Diphenylphosphinoylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide Chemical Properties

Melting point:

185-187°C

Boiling point:

679.1±65.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

pka

-0.57±0.10(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C28H29FN3O3PS/c1-20(2)26-25(19-36(33,23-11-7-5-8-12-23)24-13-9-6-10-14-24)27(21-15-17-22(29)18-16-21)31-28(30-26)32(3)37(4,34)35/h5-18,20H,19H2,1-4H3

InChIKey

CVRDGWDBQZPJJI-UHFFFAOYSA-N

SMILES

CS(N(C1=NC(C(C)C)=C(CP(C2=CC=CC=C2)(C2=CC=CC=C2)=O)C(C2=CC=C(F)C=C2)=N1)C)(=O)=O

N-[5-(Diphenylphosphinoylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide Usage And Synthesis

Uses

An intermediate in the production of Rosuvastatin (R700500) derivatives.

Synthesis

Under argon protection, ethyldiphenylphosphite (12.6 g, 55 mmol) was added to a solution of 5-(bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine (15.2 g, 36.6 mmol) in toluene (370 mL), and the reaction mixture was stirred for 3 hours at 60 °C. Upon completion of the reaction, the mixture was concentrated. The residue was dissolved in toluene (10 mL), hexane (10 mL) was added and the product N-[5-(diphenylphosphinoylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide precipitated as a colorless powder, which was collected by filtration to give 14.3 g (73% yield). The product was structurally confirmed by nuclear magnetic resonance hydrogen (1H NMR, 300 MHz, CDCl3), carbon (13C NMR, 75 MHz, CDCl3) and phosphorus (31P NMR, 121 MHz, CDCl3) spectra.

References

[1] Patent: WO2004/103977, 2004, A2. Location in patent: Page 24-25
[2] Patent: WO2012/2741, 2012, A2. Location in patent: Page/Page column 20
[3] Organic Letters, 2018, vol. 20, # 11, p. 3286 - 3290

N-[5-(Diphenylphosphinoylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide(289042-10-0)Related Product Information

• tert-Butylchlorodiphenylsilane
• p-Toluenesulfonamide
• Diphenylphosphine
• Benzenesulfonamide
• Diphenylsilane
• Sulfanilamide
• Chlorodiphenylphosphine
• Phosphonium, [[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]me
• Diphenyl 4-(4-Fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonyl)amino-pyrimidin-5-yl -methyl]phosphine Oxide-D6
• (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate
• tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate
• tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate
• tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate
• (4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester
• 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-n-methylsulfonyl)amino]pyrimidine-5-yl-methanol
• (4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate
• 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidinyl-5-yl-formyl
• N-Methyl methanesulfonamide