5-(Bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine Chemical Properties

Boiling point:

531.2±60.0 °C(Predicted)

Density 

1.466

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.77±0.10(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

799842-07-2(CAS DataBase Reference)

5-(Bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine Usage And Synthesis

Uses

5-(Bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine is an impurity of Rosuvastatin (R700500), which is a selective, competitive HMG-CoA reductase inhibitor.

Synthesis

General procedure for the synthesis of 5-(bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidines from compound (CAS:925422-06-6): 1. N-[5-hydroxymethyl-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (50.0 g) and 48% aqueous hydrogen bromide solution (130.0 mL) were added to the reactor. 2. The reaction mixture was stirred at 80 °C for 15 h. The progress of the reaction was monitored by thin-layer chromatography (unfolding agent: ethyl acetate/hexane=1:2). 3. Upon completion of the reaction, the mixture was cooled to 20 °C and stirring was continued for 1 h at this temperature. 4. The product was collected by filtration under reduced pressure and the resulting white solid was washed with deionized water (500.0 mL). 5. The washed solid was dried under reduced pressure to afford N-[5-bromomethyl-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide as a white solid (55.3 g, 94% yield). 6. The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3) with the following chemical shifts (ppm): 1.35 (d, 6H), 3.48 (m, 1H), 3.49 (s, 3H), 3.56 (s, 3H), 4.48 (q, 2H), 7.23 (t, 2H), 7.81 (q, 2H).

References

[1] Patent: WO2012/2741, 2012, A2. Location in patent: Page/Page column 19

5-(Bromomethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine(799842-07-2)Related Product Information

• Methanol
• Methylparaben
• N-Acetylsulfanilyl chloride
• 3,4'-DIAMINODIPHENYLMETHANE
• Methyl acrylate
• Isopropyl alcohol
• Basic Violet 1
• Lithium diisopropylamide
• ISOPROPYL LAURATE
• Isopropyl acetate
• Kresoxim-methyl
• Sulfanilamide
• Acetonitrile
• Methyl
• Phosphonium, [[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]me
• Rosuvastatin Impurity 65
• Rosuvastatin ethyl ester
• Rosuvastatin Impurity 81