5-(Trifluoromethyl)uracil

White to faintly yellow crystalline powder

0.11 g (1.0 mmol) of uracil was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. 0.055 g (0.5 mmol) of uracil was weighed and placed in a two-neck flask and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 1.0 ml of a 1 N dimethyl sulfoxide solution of sulfuric acid, 0.5 ml of a 2.1 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.1 ml of a 30percent hydrogen peroxide aqueous solution and 0.15 ml of a 1.0 mol/l aqueous solution of iron(II) sulfate, and the mixture was stirred for 20 minutes. During the stirring, the temperature of the reaction system rose up in the range of from 40°C to 50°C. Thereafter, the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (In a 25 mL reaction tube, Add Cs2CO3 (0.8 mmol), Compound A-1 (0.4 mmol, 1 equivalent), After replacing argon three times, add 1 mL of dimethyl sulfoxide (DMSO).100 μL (1.2 mmol) of Compound B in DMSO was injected.After stirring for 12 hours under blue light, Compound C-1, The yield was 81percent.0.11 g (1.0 mmol) of uracil was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 0.21 ml of a 42percent tetrafluoroboric acid aqueous solution, 2.0 ml of dimethyl sulfoxide, 3.0 ml of a 2.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.3 ml of a 1.0 mol/l aqueous solution of ferric tetrafluoroborate and 0.2 ml of a 30percent hydrogen peroxide aqueous solution. The mixture was stirred at 40 to 50°C for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (0.11 g (1.0 mmol) of uracil was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with trifluoromethyl iodide. 1.1 g (10 mmol) of uracil was weighed and placed in a 100 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 20 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 22.5 ml of dimethyl sulfoxide, 7.5 ml of a 2.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 2.0 ml of a 30percent hydrogen peroxide aqueous solution and 3.0 ml of a 1.0 mol/l aqueous solution of ferric sulfate. The mixture was stirred at 40 to 50°C for 30 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (0.11 g (1.0 mmol) of uracil was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with trifluoromethyl iodide. 0.11 g (1.0 mmol) of uracil was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 3.0 ml of a 2.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.12 g of hydrogen peroxide-urea composite and 0.3 ml of a 1 mol/l aqueous solution of ferric sulfate. The mixture was stirred at 40 to 50°C for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyl uracil ([00234] Uracil (28.0 mg, 0.250 mmol, 1.00 eq), K2S208 (270 mg, 1.00 mmol, 4.00 eq) and Cu(OAc)0.11 g (1.0 mmol) of uracil and 0.028 g (0.5 mmol) of iron powder were weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide and 0.2 ml of a 30percent hydrogen peroxide aqueous solution. The mixture was stirred at 40 to 50°C for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (The compound of claim 1, where B is selected from the group consisting of: ... 5-fluoro-2, 4-dioxopyrimidine, 5-chloro-2, 4-dioxopyrimidine, 5-bromo-2, 4-dioxopyrimidine, 5-iodo-2, 4-dioxopyrimidine, and 5-trifluoromethyl-2, 4-dioxopyrimidine.Particularly preferred inactivators of uracil reductase for use in accordance with the invention are 5-ethynyluracil and 5-propynyluracil. other inactivators for such use include:- ... 5-(l-chlorovinyl)uracil 5-iodouracil 5-hex-1-ynyluracil 5-vinyluracil Particularly preferred uracil derivatives which form part of the compounds as hereinbefore defined are 5-ethynyluracil and 5-propynyluracil. Other such inactivators include: ... 5-(1-chlorovinyl) uracil 5-iodouracil 5-hex-1-ynyluracil 5-vinyluracil Typical examples of the compound of formula (I) provided by the process of this invention are given below. 5-trifluoromethyldihydrouracil, 5-trifluoromethyldihydro-2-thiouracil, 1-methyl-5-trifluoromethyldihydrouracil, 1-methyl-5-trifluoromethyldihydro-2-thiouracil, 3-methyl-5-trifluoromethyldihydroouracil, 3-methyl-5-trifluoromethyldihydro-2-thiouracil, 1, 3-dimethyl-5-trifluoromethyldihydrouracil, 1, 3-dimethyl-5-trifluoromethyldihydro-2-thiouracil, 3-phenyl-5-trifluoromethyldihydrouracil, ...Formation of

Molecular Weight:180.08
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Exact Mass:180.01466183
Monoisotopic Mass:180.01466183
Topological Polar Surface Area:58.2
Heavy Atom Count:12
Complexity:268
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes