1150560-59-0

Basic information

• Product Name: 5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione
• Synonyms: 5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione;elagolix intermediate 6;5-(2-fluoro-3-methoxyphenyl)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione;Eelagolix-1;Eelagolix int1;Eelagolix intermediate;EOS-61868
• CAS NO: 1150560-59-0
• Molecular Formula: C₂₀H₁₅F₅N₂O₃
• Molecular Weight: 426.336716
• Mol File: 1150560-59-0.mol

Chemical Properties

• Appearance: /
• Density: 1.401±0.06 g/cm3(Predicted)
• PKA: 8.61±0.40(Predicted)
• CAS DataBase Reference: 5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione(1150560-59-0)
• EPA Substance Registry System: 5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione(1150560-59-0)

Safety Data

• Hazardous Substances Data: 1150560-59-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione is used as an intermediate in organic synthesis. Its unique structure allows it to be a valuable building block for the creation of more complex molecules, which can be utilized in various industries, including pharmaceuticals and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione serves as an intermediate in the synthesis of Elagolix, a gonadotropin-releasing hormone antagonist (GnRH). Elagolix is used in the treatment of endometriosis, a painful disorder that affects the uterus. The compound's role in the synthesis of Elagolix highlights its importance in the development of therapeutic agents for various medical conditions.
Used in Laboratory Research and Development:
5-(2-Fluoro-3-methoxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methyl-2,4(1H,3H)-pyrimidinedione is also utilized in laboratory research and development processes. Its unique chemical properties make it a valuable tool for scientists and researchers working on the discovery and development of new drugs and materials. The compound's versatility in organic synthesis and its potential applications in the pharmaceutical industry make it an essential component in the research and development of novel therapeutic agents and other advanced materials.

Synthesis

To a reactor was charged l-(2-fluoro-6-trifluoromethyl-benzyl)-5-iodo-6-methyl- lH-pyrimidine-2,4-dione Ib (5.0 kg), 2-fluoro-3-methoxyphenylboronic acid (2.58 kg), and acetone (5.5 L). The mixture was agitated and a potassium hydroxide/water solution (2.658 kg/19.0 L) was charged. The reactor contents were degassed for 30-60 min, then the internal temperature was adjusted to 40 0C. l,l-(bis-di-t-butylphosphino)ferrocene palladium dichloride (11.4 g) was added to the reactor and the contents mixed with jacket temperature set to 45 0C until the reaction was complete (2.5 hr). The reaction mixture was cooled to 20-30 0C. Celite (1.25 kg) was charged to the reactor and stirred for more than one hour and the mixture was filtered through a Celite pad (0.51 kg). The reactor and Celite cake were washed with acetone/water/KOH (2.6 L/7.5 L/0.38 kg). The filtered solutions were passed through a line filter and added over a period of 1-1.5 hr to a mixture of THF/AcOH/Water (15.0 L/7.53 L/5.0 L) maintained at 62 0C. The reactor contents were cooled to 20 0C over 2-3 hr. The mixture was filtered and the cake washed with 60:40 water/MeOH (2 x 12.6 L) followed by methanol (2 x 16 L). The solid was dried in a vacuum oven at 65 0C for 18 hr to provide 5-(2-fluoro-3-methoxy- phenyl)-l-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-lH-pyrimidine-2,4-dione Ic (4.312 kg, 87 % molar yield) as an off-white solid. LCMS (ESI) m/z 427.1 (MH+). If necessary, the material may be solubilized, re-treated with Celite, and crystallized as above to increase purity.

Upstream product

• 1150560-54-5 1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione 
• 352303-67-4 (2-fluoro-3-methoxyphenyl)boronic acid 
• 830346-46-8 N-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}urea 
• 15018-56-1 5-bromo-6-methyluracil 
• 239087-08-2 2-(bromomethyl)-1-fluoro-3-(trifluoromethyl)benzene 
• 830346-48-0 5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione 
• 295376-21-5 2-fluoro-3-methoxy-1-bromobenzene 
• 830346-47-9 1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-2,4(1H,3H)-pyrimidinedione 
• 401-80-9 3-fluoro-trifluoromethylbenzene 
• 60611-24-7 2-fluoro-6-(trifluoromethyl)benzaldehyde 
• 581072-15-3 2-fluoro-6-(trifluoromethyl)benzaldehyde oxime 
• 643088-07-7 2-fluoro-6-(trifluoromethyl)benzylamine hydrochloride 
• 239087-06-0 (2-fluoro-6-(trifluoromethyl) phenyl)methanamine 
• 1080673-30-8 2-fluoro-1-iodo-3-methoxybenzene 

Downstream Products

• 830346-50-4 3-[(2R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-2,4(1H,3H)-pyrimidinedione trifluoroacetate 
• 830346-51-5 (R)-(2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)carbamic acid tert-butyl ester 
• 832720-84-0 4-((R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-trifluoromethylbenzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidine-1-yl]-1-phenylethylamino)butyric acid ethyl ester 
• 834153-87-6 4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid 

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