1-[2-fluoro-6-(trifluoromethyl)benzyl]-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione CAS#: 1150560-54-5; ChemWhat Code: 1052789

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name1-[2-fluoro-6-(trifluoromethyl)benzyl]-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione
IUPAC Name1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-5-iodo-6-methylpyrimidine-2,4-dione
Molecular StructureStructure of 1-[2-fluoro-6-(trifluoromethyl)benzyl]-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione CAS 1150560-54-5
CAS Registry Number 1150560-54-5
EINECS NumberNo data available
MDL NumberMFCD19441362
Beilstein Registry NumberNo data available
Synonyms1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione, 1-[2-fluoro-6-(trifluoromethyl)benzyl]-5-iodo-6-methyl-3H-pyrimidine-2,4-dione, 1-(2-fluoro-6-trifluoromethyl-benzyl)-5-iodo-6-methyl-1H-pyrimidine-2,4-dione;CAS Number: 1150560-54-5
Molecular FormulaC13H9F4IN2O2
Molecular Weight428.121
InChIInChI=1S/C13H9F4IN2O2/c1-6-10(18)11(21)19-12(22)20(6)5-7-8(13(15,16)17)3-2-4-9(7)14/h2-4H,5H2,1H3,(H,19,21,22)
InChI KeyTZBUKGISILNJCR-UHFFFAOYSA-N
Canonical SMILESCC1=C(C(=O)NC(=O)N1CC2=C(C=CC=C2F)C(F)(F)F)I
Patent Information
Patent IDTitlePublication Date
CN110437159Preparation method of gonadotropin releasing hormone antagonist intermediate and antagonist sodium (by machine translation)2019
WO2009/62087PROCESSES FOR THE PREPARATION OF URACIL DERIVATIVES2009

Physical Data

AppearanceWhite or off-white powder
SolubilityNo data available
Flash PointNo data available
Refractive indexNo data available
SensitivityNo data available

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzOriginal Text (NMR Spectroscopy)
Chemical shifts1Hdimethylsulfoxide-d6300NMR (400 MHz, DMSO-d6) d 11.75 (s, 1H), 77.67-7.61 (m, 1H), 7.59-7.50 (m, 2H), 5.39 (s,1H), 2.56 (s, 3H).
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Temperature (IR Spectroscopy), °C
Bandspotassium bromide 27
SpectrumCCl414.85 – 54.85
3-Aminopyridine CAS#: 462-08-8 IR3-Aminopyridine CAS#: 462-08-8 IR
Description (Mass Spectrometry)Comment (Mass Spectrometry)
ESI (Electrospray ionisation), LCMS (Liquid chromatography mass spectrometry)Molecular peak

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 1-[2-fluoro-6-(trifluoromethyl)benzyl]-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione CAS 1150560-54-5
Route of Synthesis (ROS) of 1-[2-fluoro-6-(trifluoromethyl)benzyl]-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione CAS 1150560-54-5
ConditionsYield
With Iodine monochloride In methanol at 50℃; for 6h;

Experimental Procedure
To a 250 mL three-neck round bottom flask was charged l-(2-fluoro-6- trifluoromethyl-benzyl)-6-methyl-lH-pyrimidine-2,4-dione Ia (25.0 g) and methanol (250 mL). Iodine monochloride (30.9 g) was charged over 2.5 min. The mixture was heated at 50 0C for 3 hours. After cooling to ambient temperature, the mixture was filtered. The cake was re-slurried in methanol (250 mL) and heated to 50 C for 3 hours. After cooling to ambient temperature, the mixture was filtered and the filter cake was washed with methanol (50 mL). The off-white solid was dried in a vacuum oven at 50 C to provide l-(2-fluoro-6-trifluoromethyl-benzyl)-5-iodo-6-methyl-lH-pyrimidine-2,4- dione Ib (32.5 g, 90% yield). LCMS (ESI) m/z 429.3 (MH+). The material may be re- slurried in MeOH as needed.		90%
With N-iodo-succinimide; acetic acid at 50℃; for 1h;

Experimental Procedure
To a 50 mL round botom flask was added AcOH (20 mL), compound IX (2 g) and N-Iodosuccinimide (1.5 g). The reaction mixture was heated to 50 °C for lh. After completion of the reaction, LLO (10 mL) was added to the reaction mixture. The resulting suspension was filtered. The cake was washed with MeOH (4 mL). The solid was slurried with MeOH (20 mL) to give the product as a white solid (2.3 g, 82% yield, 96.1% purity). NMR (400 MHz, DMSO-d6) d 11.75 (s, 1H), 77.67-7.61 (m, 1H), 7.59-7.50 (m, 2H), 5.39 (s, 1H), 2.56 (s, 3H).		82%

Safety and Hazards

Pictogram(s)exclamation-markhealth-hazard
SignalWarning
GHS Hazard StatementsH302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (33.33%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H315 (66.67%): Causes skin irritation [Warning Skin corrosion/irritation]
H320 (66.67%): Causes eye irritation [Warning Serious eye damage/eye irritation]
H332 (33.33%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H361 (66.67%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesP201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationNo data available
Under the room temperature and away from light
HS CodeNo data available
StorageUnder the room temperature and away from light
Shelf Life1 year
Market PriceUSD
Druglikeness
Lipinski rules component
Molecular Weight428.125
logP3.322
HBA4
HBD1
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)49.41
Rotatable Bond (RotB)3
Matching Veber Rules2
Use Pattern
1-[2-fluoro-6-(trifluoromethyl)benzyl]-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione CAS#: 1150560-54-5 is usually used as an intermediate of API, Elagolix

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