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[ CAS No. 66-22-8 ]

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Chemical Structure| 66-22-8
Chemical Structure| 66-22-8
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CAS No. :66-22-8 MDL No. :MFCD00006016
Formula : C4H4N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :112.09 g/mol Pubchem ID :1174
Synonyms :

1. Uracil

Safety of [ 66-22-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 66-22-8 ]

  • Upstream synthesis route of [ 66-22-8 ]
  • Downstream synthetic route of [ 66-22-8 ]

[ 66-22-8 ] Synthesis Path-Upstream   1~65

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YieldReaction ConditionsOperation in experiment
92% at 50 - 55℃; for 3 h; Inert atmosphere Nitric acid solution (5.34 mL, 120 mmol, 70percent solution) was added drop-wise to a concentrated sulfuric acid (19.7 mL, 360 mmol, 98percent solution) during which time the temperature did not exceed 50 °C. Pyrimidine-2,4(1H,3H)-dione 5 (7.204 g, 60 mmol) was added in several portions to the stirred solution ensuring the temperature did not exceed 50 °C. The reaction was heated to 55 °C for 3 hours, and then cooled below room temperature and quenched with ice-water (38 mL). The resulting white precipitate was collected by filtration, washed with a small amount of ice water and dried under reduced pressure at 55 °C to yield a white solid 6 (8.658 g, 55.11 mmol, 92percent).m.p. >288 oC decomposition; Rf 0.00 (1/10, ethyl acetate/hexane); IR (ZnSe cell , solid) vmax: 3142-2811 (m, br, O-H/N-H/C-H), 1732 (s, C=O), 1677, 1624 (s, NO2), 1417 (m, C-H), 1356 (m, NO2), 1318 (s, aromatic R2NH/R3N), 1234 (s, -OH), 975, 832 (w, aromatic ring bending); 1H NMR (500 MHz, d6-DMSO): δ 8.84 (1H, s, 6-CH) ppm; 13C NMR (125 MHz, d6-DMSO): δ 155.5 (4-C=O), 149.8 (6-CH), 147.9 (2-C=O), 125.1 (5-CNO2) ppm.
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 29 - 34
[2] American Chemical Journal, 1905, vol. 33, p. 443
[3] American Chemical Journal, 1908, vol. 40, p. 31[4] Journal of Biological Chemistry, 1908, vol. 4, p. 410
[5] Journal of the American Chemical Society, 1919, vol. 41, p. 786
[6] Journal of the Chemical Society, 1951, p. 1565,1568[7] Journal of the Chemical Society, 1953, p. 1646
[8] Journal of Applied Chemistry, 1952, vol. 2, p. 239
[9] Tetrahedron Letters, 2011, vol. 52, # 42, p. 5521 - 5524
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Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 95, p. 16 - 22
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Reference: [1] Acta Chemica Scandinavica (1947-1973), 1957, vol. 11, p. 17,20
[2] The Journal of biological chemistry, 1957, vol. 226, # 2, p. 1093 - 1101
[3] The Journal of biological chemistry, 1957, vol. 226, # 2, p. 1093 - 1101
[4] ChemCatChem, 2018, vol. 10, # 2, p. 439 - 448
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Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 36, p. 14452 - 14459
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Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 36, p. 14452 - 14459
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1924, vol. 178, p. 812
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YieldReaction ConditionsOperation in experiment
0.1 mg With manganese(II) chloride tetrahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
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YieldReaction ConditionsOperation in experiment
0.18 mg With ferric sulfate nonahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
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  • [ 302-72-7 ]
YieldReaction ConditionsOperation in experiment
0.12 mg With magnesium sulfate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
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  • [ 57-13-6 ]
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YieldReaction ConditionsOperation in experiment
1.6 mg With copper(II) choride dihydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
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YieldReaction ConditionsOperation in experiment
72.3% at 110℃; for 3.5 h; Inert atmosphere In a 500 ml, two-necked, round-bottom flask equipped with a condenser, uracil (100 g, 0.82 mol) was dissolved in phosphorous oxychloride (400 ml). The solution was refluxed with stirring for 3.5 h at 110 °C. The residual phosphorous oxychloride was removed in vacuo at 50 °C and the remaining oil was poured into 50 g of ice, followed by extraction with chloroform (3 * 50 ml). The combined organic extract was washed with dilute sodium carbonate solution and dried over anhydrous sodium sulfate. 2,4-Dichloropyrimidine was obtained by removal of the solvent.
80 g at 0℃; for 4 h; Reflux To a mixture of Ν,Ν-dimethyl aniline (140 gm) and uracil (100 gm) was added phosphorous oxychloride (342 gm) slowly at 0°C. The contents were then heated to reflux and maintained for 4 hours. The solution was then cooled to room temperature, then transferred into ice water and stirred for 1 hour. The resulting precipitate was filtered and washed with water. The solid thus obtained was recrystallized from hexane to give 80 gm of 2,4-dichloro pyrimidine.
80 g at 0℃; for 4 h; Reflux Preparative Example 1 Preparation of 2,4-dichloro pyrimidine [0078] To a mixture of N,N-dimethyl aniline (140 gm) and uracil (100 gm) was added phosphorous oxychloride (342 gm) slowly at 0° C. The contents were then heated to reflux and maintained for 4 hours. The solution was then cooled to room temperature, then transferred in to ice water and stirred for 1 hour. The resulting precipitate was filtered and washed with water. The solid thus obtained was recrystallized from hexane to give 80 gm of 2,4-dichloro pyrimidine.
80 g at 0℃; for 4 h; Reflux Step-I:
Preparation of 2,4-dichloro pyrimidine
To a mixture of N,N-dimethyl aniline (140 gm) and uracil (100 gm) was added phosphorous oxychloride (342 gm) slowly at 0° C.
The contents were then heated to reflux and maintained for 4 hours.
The solution was then cooled to room temperature, then transferred into ice water and stirred for 1 hour.
The resulting precipitate was filtered and washed with water.
The solid thus obtained was recrystallized from hexane to give 80 gm of 2,4-dichloro pyrimidine.

Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 2, p. 435 - 448
[2] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527
[3] Polyhedron, 2014, vol. 81, p. 316 - 322
[4] Dalton Transactions, 2012, vol. 41, # 8, p. 2477 - 2485
[5] Chemische Berichte, 1905, vol. 38, p. 1690
[6] Journal of the Chemical Society, 1951, p. 1565,1568[7] Journal of the Chemical Society, 1953, p. 1646
[8] Journal of the Chemical Society, 1951, p. 1218,1221
[9] Journal of the American Chemical Society, 1930, vol. 52, p. 1152,1156; vgl. H 24 80
[10] Yakugaku Zasshi, 1950, vol. 70, p. 137[11] Chem.Abstr., 1950, p. 5886
[12] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 6, p. 1831 - 1835
[13] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1111 - 1114
[14] Tetrahedron, 2009, vol. 65, # 1, p. 247 - 252
[15] Patent: WO2012/147091, 2012, A2, . Location in patent: Page/Page column 7
[16] Patent: WO2013/38425, 2013, A1, . Location in patent: Page/Page column 7; 8
[17] Heterocycles, 2012, vol. 86, # 2, p. 1583 - 1590
[18] Patent: US2014/228385, 2014, A1, . Location in patent: Paragraph 0078
[19] Patent: US2014/350038, 2014, A1, . Location in patent: Paragraph 0080; 0081
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Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 10, p. 4149 - 4153
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 4, p. 986 - 991
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Reference: [1] Patent: CN108467368, 2018, A, . Location in patent: Paragraph 0014; 0015
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Reference: [1] Journal of the Chemical Society, 1957, p. 323,325
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984, # 4, p. 601 - 608
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Reference: [1] Synthesis, 1988, # 10, p. 771 - 775
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YieldReaction ConditionsOperation in experiment
100% With potassium hydroxide In water at 50 - 52℃; for 68 h; Example 1a
5-(Hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione
A 2-L, three-necked flask equipped with a mechanical stirrer, thermometer, condenser, and nitrogen-inlet bubbler was charged with uracil (185.0 g, 1650 mmol) (Aldrich), paraformaldehyde (61.50 g, 2050 mmol as formaldehyde) (Aldrich), and a solution of potassium hydroxide (86.9percent, 59.95 g, 928.5 mmol) (Aldrich) in water (1.445 L).
The mixture was stirred at 50-52° C. for 68 h. TLC analysis indicated complete reaction.
After concentration at 60° C./14 mmHg to a volume of ca.
500 mL, the residue was diluted with acetone (500 mL).
The resulting precipitate was collected by filtration, washed with acetone, and dried by suction, then at 50° C./25 mmHg to give crude 5-(hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione (250 g) as a white solid.
The combined mother liquor and washes were concentrated to a volume of ca. 100 mL and a solution of hydroxylamine hydrochloride (27.52 g, 396.0 mmol, Aldrich) in water (100 mL) was added.
The resulting precipitate was collected by filtration, washed with acetone, and dried by suction to give second crop of crude 5-(hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione (34 g) as a white solid.
The two lots were combined (244 g, 4percent overweight) and used directly in the next step.
98% With potassium hydroxide In water at 0 - 55℃; for 36 h; To a mixture of 1H-pyrimidine-2,4-dione (20 g, 178.4 mmol) in aqueous solution of potassium hydroxide (8.0 g, 142.7 mmol) in water (160.0 mL), paraformaldehyde (6.96 g, 231.9 mmol) was added portion-wise at 0° C. The resulting reaction mixture was stirred at 55° C. for 36 h. After completion, the reaction was cooled to room temperature and concentrated to rd of the volume under reduced pressure to yield a white thick mass. The residue was diluted with acetone (150 mL) and stirred at 25° C. for 15 min at which point a precipitate formed. The solid was filtered and washed with acetone (3×50 mL) and dried under vacuum to afford S9-1 (25 g, 98percent) as a white solid. MS m/z (M−H): 140.9.
73% With triethylamine In water at 60℃; for 16 h; Inert atmosphere A suspension of uracil (2.5 g, 22.3 mmol) and para-formaldehyde (2.0 g, 66.9 mmol) in H2O (75 mL)was treated with NEt3 (4.6 mL, 33.4 mmol) and heated with stirring at 60 °C for 16 h. The mixture wasrotary evaporated, and the residue triturated with H2O and EtOH (1:1, 20 mL), stirred for 1 h at 0 °C,filtered and washed with cold EtOH to yield 5-hydroxymethyluracil (20) (2.3 g, 73 percent) as a white solid
44%
Stage #1: With potassium hydroxide In water at 50℃; for 20 h;
Stage #2: With hydrogenchloride In water
A mixture of uracil (3.6 g, 32.1 mmol), formaldehyde (37percent in water) (3.25 ml), KOH (1.4 g, 25 mmol) in water (45 ml) was stirred at 50° C. for 20 h. The reaction was acidified with 1 N HCl to give a white precipitate. The solids were collected dried under vacuum to give the 5-(hydroxymethyl)-2,4(1H,3H)-pyrimidinedione (2.01 g, 44percent) as a white solid.
39% at 20 - 50℃; for 108 h; Uracil (10.0 g, 89.2 mmol, 1.0 eq.) and paraformaldehyde (3.24 g, 107 mmol, 1.2 eq.) were treated with KOH (0.5 M, 133 ml) and the mixture heated at 50 °C for 8 hours 30 minutes, stirred at rt for 64 hours then heated at 50°C for 24 hours. The mixture was cooled to 0°C in an ice bath and acidified to pH 6 with HC1 (conc). The precipitate wasfiltered off, washed with water and oven dried providing the title compound (4.93 g,39percent) as a white solid.‘HNMR (400 MHz, DMSO)6 11.05 (s, IH), 10.71 (s, 1H), 7.24(s, IH),4.85 (t,J=5.5 Hz, 1H), 4.11 (dd, J 5.5, 1.1 Hz, 2H). Rf = 0.10 (50:8:1 DCM:EtOH:NH3)
46.0 g at 55℃; Intermediate 1 [00353j A 1-L, three-necked flask equipped with a mechanical stirrer, was charged with uracil (45.0 g, 401 mmol) and paraformaldehyde (14.5 g, 483 mmol). A solution of potassium hydroxide (0.5 M, 600 mL, 0.30 mol) was added in one portion. The resulting mixture was stirred at 55 °C overnight. The mixture was cooled in an ice-water bath and the pH was adjusted to 6 with 12 N HC1. The resulting precipitate was collected by filtration and dried to afford the title compound (46.0 g) as a white solid which was used in the next step without further purification. ‘H NMR (400 MHz, DMSO-d6): ö 4.12 (d, 2H), 4.78 (t, 1H), 7.24 (s, 1H), 10.64 (s, 1H), 10.98 (s, 1H).
16.26 g at 52℃; for 20.5 h; (2) Uracil (13.5 g, 100 mmol) and paraformaldehyde (4.5 g, 120 mmol) were dissolved in 150 mL of 0.5 mol / L After the potassium hydroxide solution was stirred for half an hour, it was stirred in a water bath at 52 ° C for about 20 hours. The thin layer analysis showed that the raw material completely disappeared. Most of the water is removed with a rotary evaporator so that the inner volume of the flask is approximately 1/3 of the original volume, After adding an equal amount of acetone recrystallized at 0 ~ 5 °C , 3 hours, suction filtration, washing, pumping dry, vacuum drying, weighing. Product is a white solid 16.26g

Reference: [1] Patent: US2004/38995, 2004, A1, . Location in patent: Page/Page column 4-6
[2] Synlett, 2002, # 12, p. 2043 - 2044
[3] Patent: US2016/75720, 2016, A1, . Location in patent: Paragraph 0321
[4] Canadian Journal of Chemistry, 2007, vol. 85, # 4, p. 302 - 312
[5] Canadian Journal of Chemistry, 2005, vol. 83, # 10, p. 1731 - 1740
[6] Tetrahedron, 2003, vol. 59, # 26, p. 4733 - 4738
[7] Chemical Communications, 2017, vol. 53, # 36, p. 5013 - 5016
[8] Chemistry - A European Journal, 2014, vol. 20, # 31, p. 9753 - 9761
[9] Journal of Organic Chemistry, 1998, vol. 63, # 24, p. 9117 - 9121
[10] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3293 - 3297
[11] Patent: US2003/229081, 2003, A1, . Location in patent: Page 14; 17
[12] Patent: WO2018/25043, 2018, A1, . Location in patent: Page/Page column 23
[13] Journal of the American Chemical Society, 1959, vol. 81, p. 2521,2525
[14] Journal of the American Chemical Society, 1959, vol. 81, p. 2521,2525
[15] Patent: US2004/122029, 2004, A1, . Location in patent: Page/Page column 10
[16] Patent: US2004/204427, 2004, A1, . Location in patent: Page/Page column 6; 9
[17] European Journal of Pharmacology, 2011, vol. 672, # 1-3, p. 30 - 37
[18] Patent: WO2014/144737, 2014, A1, . Location in patent: Paragraph 00353
[19] Arkivoc, 2016, vol. 2017, # 2, p. 149 - 161
[20] Chemical Communications, 2017, vol. 53, # 81, p. 11169 - 11172
[21] Patent: CN104803924, 2017, B, . Location in patent: Paragraph 0047; 0062; 0066
  • 22
  • [ 66-22-8 ]
  • [ 4433-40-3 ]
Reference: [1] Patent: US5859014, 1999, A,
[2] Patent: EP748800, 1996, A3,
  • 23
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  • [ 1820-81-1 ]
Reference: [1] Canadian Journal of Chemistry, 1982, vol. 60, p. 554 - 557
[2] Journal of Organic Chemistry, 1990, vol. 55, # 16, p. 4928 - 4933
[3] Tetrahedron Letters, 1992, vol. 33, # 50, p. 7779 - 7782
[4] Chemistry Letters, 1987, p. 2311 - 2312
  • 24
  • [ 66-22-8 ]
  • [ 1820-81-1 ]
  • [ 2072-83-5 ]
Reference: [1] Chemistry Letters, 1986, p. 1319 - 1322
[2] Chemistry Letters, 1986, p. 1319 - 1322
  • 25
  • [ 128-09-6 ]
  • [ 66-22-8 ]
  • [ 1820-81-1 ]
Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3146
  • 26
  • [ 128-09-6 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • [ 66-22-8 ]
  • [ 1820-81-1 ]
Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3146
  • 27
  • [ 68-12-2 ]
  • [ 66-22-8 ]
  • [ 10070-92-5 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: at 5℃; for 0.5 h;
Stage #2: at 5℃; for 2 h;
In the reaction bottle,Add solvent DMF (560 mL),Cool down to 5 ° C,Slowly add phosphorus oxychloride (230g),Control the reaction temperature of the mixed system to not exceed 5 ° C,After the addition of phosphorus oxychloride,Add aluminum trichloride (133g),Stir for 30min,Then, 112 g (1 mol) of uracil in a solid form was added in portions to the above mixed system.Control the reaction temperature not to exceed 5 ° C,After stirring for 2 hours,Slowly warm to room temperature and continue to stir the reaction until the raw materials disappear.After the reaction is over,Adding the reactants to the rapidly stirred ice-water mixture,Precipitating pyrimidine-5-formaldehyde solid 133g,Yield 95percent,The purity is 99.5percent.
Reference: [1] Patent: CN108276345, 2018, A, . Location in patent: Paragraph 0008; 0009; 0010; 0011; 0012; 0013
  • 28
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 156-81-0 ]
  • [ 113-00-8 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 57-13-6 ]
YieldReaction ConditionsOperation in experiment
0.1 mg With manganese(II) chloride tetrahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 29
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 156-81-0 ]
  • [ 120-89-8 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
YieldReaction ConditionsOperation in experiment
1.6 mg With copper(II) choride dihydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 30
  • [ 77287-34-4 ]
  • [ 23147-58-2 ]
  • [ 1455-77-2 ]
  • [ 849585-22-4 ]
  • [ 328-42-7 ]
  • [ 110-15-6 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 57-13-6 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 31
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 849585-22-4 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 32
  • [ 2314-97-8 ]
  • [ 66-22-8 ]
  • [ 54-20-6 ]
YieldReaction ConditionsOperation in experiment
93% With iron(III) sulfate; dihydrogen peroxide In water; dimethyl sulfoxide at 40 - 50℃; for 0.333333 h; 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, 1.0 ml of a 2.1 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.2 ml of a 30percent hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 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 (19F-NMR yield: 94percent) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard.
5-Trifluoromethyluracil was obtained as a white solid (0.17 g, yield: 93percent) by preparative thin-layer chromatography. 1H-NMR (deuterated acetone): δ8.09(s, 1H), 10.5(brs, 2H).
13C-NMR (deuterated acetone): δ104. 0 (q, JCF=32.4Hz), 123.6(q, JCF=268.2Hz), 144.2 (q, JCF=5. 9Hz), 150. 9, 160.2. 19F-NMR (deuterated acetone): δ-64.1.
MS (m/z): 180 [M]+.; EXAMPLE 9 Formation of 5-trifluoromethyluracil (19F-NMR yield: 76percent) was confirmed exactly in the same manner as in Example 1, except that the reaction was carried out in the atmosphere of air without the replacement with argon.
87% With sulfuric acid; dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water at 40 - 50℃; for 0.333333 h; 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 (19F-NMR yield: 90percent) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 5-trifluoromethyluracil was obtained as a white solid (0.16 g, yield: 87percent) in the same manner as in Example 1. 1H-NMR (deuterated acetone):δ8. 09(s, 1H), 10. 5 (brs, 2H). 13C-NMR(deuterated acetone):δ104. 0(q, JCF=32. 4Hz), 123. 6 (q, JCF=268. 2Hz), 144. 2(q, JCF=5. 9Hz), 150. 9, 160. 2. 19F-NMR(deuterated acetone):δ-64. 1. MS (m/z):180[M]+.
81% With caesium carbonate In dimethyl sulfoxide for 12 h; Inert atmosphere; Irradiation 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.
94 %Spectr. With tetrafluoroboric acid; iron(III) tetrafluoroborate; dihydrogen peroxide In water; dimethyl sulfoxide at 40 - 50℃; for 0.333333 h; 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 (19F-NMR yield: 94percent) was confirmed in the same manner as in Example 1.
0.5 %Spectr. With iron(III) sulfate; sulfuric acid; dihydrogen peroxide In 1,1'-sulfinylbisbenzene; water at 40 - 50℃; for 0.333333 h; 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.
The following materials were added thereinto:
5.0 g of diphenyl sulfoxide, 0.053 ml of concentrated sulfuric acid, 0.2 ml of a 30percent hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 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-trifluoromethyluracil (19F-NMR yield: 0.5percent) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard.
94 - 97 %Spectr. With iron(III) sulfate; sulfuric acid; dihydrogen peroxide In water; dimethyl sulfoxide at 40 - 70℃; for 0.166667 - 1.66667 h; 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 (19F-NMR yield: 94percent) was confirmed in the same manner as in Example 1.; EXAMPLE 11 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: 0.055 ml of concentrated sulfuric acid, 9 ml of dimethyl sulfoxide, 24.5 mmol of trifluoromethyl iodide, 2.0 ml of a 30percent hydrogen peroxide aqueous solution and 1.5 ml of a 1.0 mol/l aqueous solution of ferric sulfate. The mixture was stirred at 60 to 70°C for 10 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 97percent) was confirmed in the same manner as in Example 1.; EXAMPLE 12 11.2 g (100 mmol) of uracil was weighed and placed in a 300 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: 80 ml of dimethyl sulfoxide, 0.55 ml of concentrated sulfuric acid, 245 mmol of trifluoromethyl iodide, 20 ml of a 30percent hydrogen peroxide aqueous solution and 10 ml of a 1.5 mol/l aqueous solution of ferric sulfate. The mixture was stirred at 60 to 70°C for 100 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 97percent) was confirmed in the same manner as in Example 1.
0.2 %Spectr. With iron(III) sulfate; sulfuric acid; dihydrogen peroxide In butyl sulfoxide; water at 40 - 50℃; for 0.333333 h; 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.
The following materials were added thereinto:
5.0 ml of dibutyl sulfoxide, 0.053 ml of concentrated sulfuric acid, 0.2 ml of a 30percent hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 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-trifluoromethyluracil (19F-NMR yield: 0.2percent) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard.
70 %Spectr. With iron(III) sulfate; sulfuric acid; urea hydrogen peroxide adduct In water; dimethyl sulfoxide at 40 - 50℃; for 0.333333 h; 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 (19F-NMR yield: 70percent) was confirmed in the same manner as in Example 1

Reference: [1] Patent: EP1947092, 2008, A1, . Location in patent: Page/Page column 36; 37
[2] Patent: EP2080744, 2009, A1, . Location in patent: Page/Page column 6
[3] Patent: CN108484508, 2018, A, . Location in patent: Paragraph 0023; 0026; 0029; 0032; 0033; 0034; 0035; 0038
[4] Patent: EP1947092, 2008, A1, . Location in patent: Page/Page column 37
[5] Patent: EP1947092, 2008, A1, . Location in patent: Page/Page column 37
[6] Patent: EP1947092, 2008, A1, . Location in patent: Page/Page column 38
[7] Patent: EP1947092, 2008, A1, . Location in patent: Page/Page column 37
[8] Patent: EP1947092, 2008, A1, . Location in patent: Page/Page column 37
  • 33
  • [ 66-22-8 ]
  • [ 54-20-6 ]
YieldReaction ConditionsOperation in experiment
57% at 90℃; for 24 h; Inert atmosphere; Sealed tube [00234] Uracil (28.0 mg, 0.250 mmol, 1.00 eq), K2S208 (270 mg, 1.00 mmol, 4.00 eq) and Cu(OAc)2 FontWeight="Bold" FontSize="10" H20 (100 mg, 0.500 mmol, 2.00 eq) were dissolved in glacial acetic acid (2.00 mL). TMG'CF3I (0.100 mL, 0.500 mmol, 2.00 eq) was added, the reaction vessel was sealed and heated at 90 °C for 24 hours. The reaction mixture was diluted with water (50 mL) and the resulting mixture extracted with ethyl acetate (3 x 25 mL). The combined ethyl acetate extracts were dried (MgS04) and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 5percent MeOH/CH2Cl2 to afford 25.5 mg (0.142 mmol, 57percent) 12 as a white solid. [00235] R/ = 0.30 (5percent MeOH/CH2Cl2). NMR spectroscopy: 1H NMR (400 MHz, CD30D, 23 °C) δ ppm 7.93 (s, 1H), 4.60 (bs, 2H). 13C NMR (125 MHz, CD3OD, 23 °C) δ ppm 162.1, 152.5, 144.8 (q, JCF = 6 Hz), 123.9 (q, J = 269 Hz), 104.8 (q, JCF = 34 Hz). 19F NMR (376 MHz, CD3OD, 23 °C) δ ppm -64.8. Mass spectrometry: HRMS (APCI) (m/z): Calcd for [C5H3F3N202]+, [M ] : 180.0147. Found, 180.0157.
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3712 - 3716[2] Angew. Chem., 2015, vol. 127, # 12, p. 3783 - 3787,5
[3] Patent: WO2015/168368, 2015, A1, . Location in patent: Paragraph 00234; 00235
  • 34
  • [ 39971-65-8 ]
  • [ 66-22-8 ]
  • [ 54-20-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 44, p. 11868 - 11871[2] Angew. Chem., 2014, vol. 126, # 44, p. 12062 - 12065,4
  • 35
  • [ 66-22-8 ]
  • [ 54-20-6 ]
YieldReaction ConditionsOperation in experiment
32 %Spectr. With sulfuric acid; dihydrogen peroxide; iron In water; dimethyl sulfoxide at 40 - 50℃; for 0.333333 h; 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 (19F-NMR yield: 32percent) was confirmed in the same manner as in Example 1.
Reference: [1] Patent: EP1947092, 2008, A1, . Location in patent: Page/Page column 37
  • 36
  • [ 371-76-6 ]
  • [ 66-22-8 ]
  • [ 54-20-6 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1984, vol. 326, # 6, p. 985 - 993
  • 37
  • [ 75-63-8 ]
  • [ 66-22-8 ]
  • [ 54-20-6 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1988, vol. 61, p. 3531 - 3538
  • 38
  • [ 66-22-8 ]
  • [ 407-25-0 ]
  • [ 54-20-6 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1984, vol. 326, # 6, p. 985 - 993
  • 39
  • [ 3083-77-0 ]
  • [ 66224-66-6 ]
  • [ 66-22-8 ]
  • [ 5536-17-4 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 30, p. 23569 - 23577
  • 40
  • [ 66-22-8 ]
  • [ 3921-01-5 ]
YieldReaction ConditionsOperation in experiment
78.5% at 125℃; for 2 h; A mixture of phosphorus oxybromide (40.13 g, 0.14 mol) and uracil (3 g, 0.027 mol) was stirred at 125 ° C for 2 hours. The reaction was allowed to cool to room temperature and the reaction mixture was slowly poured into 500 g of ice water and washed with solid sodium bicarbonate Neutralization reaction. The aqueous phase is extracted twice with 150 ml of methylene chloride. The organic phase was dried and dried under reduced pressure to give 6.2 g of crude product,The crude product was then purified on a flash silica gel column to give 5 g of a white solid (yield: 78.5percent).
Reference: [1] Patent: CN106632077, 2017, A, . Location in patent: Paragraph 0017; 0018; 0019; 0025; 0026; 0027; 0032-0034
[2] Journal of Heterocyclic Chemistry, 2005, vol. 42, # 4, p. 509 - 513
[3] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 4, p. 1159 - 1163
  • 41
  • [ 951-78-0 ]
  • [ 69304-49-0 ]
  • [ 66-22-8 ]
  • [ 69304-47-8 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 95, p. 16 - 22
  • 42
  • [ 50-00-0 ]
  • [ 66-22-8 ]
  • [ 6623-81-0 ]
Reference: [1] Chemical Research in Toxicology, 1999, vol. 12, # 9, p. 802 - 808
  • 43
  • [ 66-22-8 ]
  • [ 999-97-3 ]
  • [ 10457-14-4 ]
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[2] Synthesis, 1985, # 4, p. 397 - 399
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  • 59
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  • 60
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18514-52-8 ]
YieldReaction ConditionsOperation in experiment
0.18 mg With ferric sulfate nonahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 61
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
YieldReaction ConditionsOperation in experiment
0.12 mg With magnesium sulfate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 62
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 849585-22-4 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 63
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 120-89-8 ]
  • [ 849585-22-4 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 18588-61-9 ]
  • [ 18514-52-8 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 64
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 65
  • [ 51-20-7 ]
  • [ 951-78-0 ]
  • [ 59-14-3 ]
  • [ 66-22-8 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 95, p. 16 - 22
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