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[ CAS No. 51953-18-5 ]

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Chemical Structure| 51953-18-5
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Product Details of [ 51953-18-5 ]

CAS No. :51953-18-5 MDL No. :MFCD00038024
Formula : C4H4N2O Boiling Point : 227.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :96.09 g/mol Pubchem ID :20695
Synonyms :

Safety of [ 51953-18-5 ]

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

Application In Synthesis of [ 51953-18-5 ]

  • Upstream synthesis route of [ 51953-18-5 ]
  • Downstream synthetic route of [ 51953-18-5 ]

[ 51953-18-5 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 51953-18-5 ]
  • [ 19808-30-1 ]
YieldReaction ConditionsOperation in experiment
91.5% With bromine In methanol; chloroform at 0℃; for 12 h; Step A:
Preparation of 5-bromopyrimidin-4(3H)-one: Bromine (16.0 mL, 312 mmol) was added to a suspension of pyrimidin-4(3H)-one (30 g, 312 mmol) in chloroform (1 L) at 0° C. Methanol (10 mL) was added and the reaction mixture was stirred for 12 hours.
The resulting solid was collected by filtration, washed with hexane and ether, and dried under vacuum to afford the title compound as a white solid (50 g, 91.5percent yield).
1H NMR (400 MHz, DMSO-d6) δ 11.15 (broad s, 1H), 8.42 (s, 1H), 8.40 (s, 1H).
3.1 g at 20℃; for 0.5 h; Inert atmosphere Step T2: 5-Bromo-3H-pyrimidin-4-one A mixture of 3H-pyrimidin-4-one (1 1 g, 114 mmol), bromine (6.5 mL, 126 mmol), and KOAc (33.7 g, 343 mmol) in AcOH (100 mL) was stirred for 30 min at rt. The resulting precipitate was collected by filtration to provide 30 g of a white solid. This solid was dissolved in CH2CI2/water, extracted with CH2CI2/MeOH (9: 1 ). The organic layer was dried (Na2S04), filtered, and concentrated to afford 3.1 g of the title compound (compound was soluble in water and stayed in the aqueous layer despite repeated extractions). tR: 0.35 min (LC-MS 2); ESI-MS: 175.0 [M+H]+ (LC-MS 2).
Reference: [1] Patent: US2007/238726, 2007, A1, . Location in patent: Page/Page column 75
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 3905 - 3912
[3] Journal of the Chemical Society, 1955, p. 3478,3481
[4] Patent: WO2013/111105, 2013, A1, . Location in patent: Page/Page column 125
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  • [ 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
  • 3
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  • [ 56-06-4 ]
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  • [ 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
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  • [ 66224-66-6 ]
  • [ 57-13-6 ]
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  • [ 302-72-7 ]
  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
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  • [ 302-72-7 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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  • [ 6554-61-6 ]
Reference: [1] Patent: WO2004/35549, 2004, A1, . Location in patent: Page 75
  • 7
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  • [ 2426-94-0 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 7, p. 1854 - 1857
  • 8
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  • [ 64264-15-9 ]
  • [ 126126-58-7 ]
  • [ 126126-57-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 8, p. 1984 - 1986
[2] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 8, p. 1984 - 1986
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 8, p. 1984 - 1986
  • 10
  • [ 77287-34-4 ]
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  • [ 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
  • 11
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  • [ 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
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  • [ 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
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
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  • [ 127-17-3 ]
  • [ 66-22-8 ]
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  • [ 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
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  • [ 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
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  • [ 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
  • 17
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  • [ 4349-07-9 ]
YieldReaction ConditionsOperation in experiment
67% With N-iodo-succinimide In acetic acid at 100℃; for 0.5 h; 10 g of 4(3H)-pyrimidone was dissolved in 156 mL of acetic acid, and 25.8 g of N-iodosuccinimide was added thereto at 70°C and heated to 100°C, followed by stirring for 30 minutes. After the reaction was completed, the mixture was cooled to room temperature then cooled in ice to induce the crystallization of the product, followed by filtering under a reduced pressure. The solid thus obtained was washed with water and dried under a reduced pressure to obtain the title compound (16 g, yield: 67percent).1H-NMR (300MHz, DMSO-d6) δ 12.88 (bs, 1H), 8.42 (s, 1H), 8.17 (s, 1H).
64% With sodium hydroxide In water at 85℃; for 16 h; To a stirred solution containing 20.2 g (0. 21 mol) of pyrimidin-4 (3H)-one and 170 mL of water was added 10.9 g (0.27 mol) of sodium hydroxide, followed by 53.3 g (0.21 mol) of iodide. The reaction mixture was heated at 85°C for 16h, then cooled to room temperature and filtered. The filter cake was washed with water, collected, and dried under reduced pressure to give 29.7g (64percent) of the TITLE COMPOUND. H-NMR (300 MHz, DMSO-d6) No. 8. 17 (s, 1H), 8.43 (s, 1H), and 12.92 (brs, 1H) ; ESIMS : 223.1 (M+H) +
44% With iodine; sodium hydroxide In water at 85℃; for 72 h; Pyrimidin-4(3H)-one (1 g, 10.41 mmol) was dissolved in 10 ml water. Sodium hydroxide (0.54 g, 13.50 mmol) and iodine (2.64 g, 10.40 mmol) were added and the reaction mixture heated at 85°C for 72 h. The reaction mixture was filtered and washed with water. The solid formed was dried in the vacuum oven to give 1.01 g (44percent yield) of the title compound. Purity 100percent.LRMS (m/z): 223 (M+1 )+
Reference: [1] Synthesis (Germany), 2012, vol. 44, # 22, p. 3496 - 3504
[2] Patent: WO2011/99764, 2011, A2, . Location in patent: Page/Page column 43
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 9, p. 2419 - 2422
[4] Patent: WO2005/16914, 2005, A1, . Location in patent: Page/Page column 45
[5] Chemical & Pharmaceutical Bulletin, 1986, vol. 34, # 7, p. 2719 - 2724
[6] Patent: WO2014/60432, 2014, A1, . Location in patent: Page/Page column 139
[7] Patent: US2002/52375, 2002, A1,
[8] Patent: US2002/52470, 2002, A1,
[9] Patent: WO2005/97162, 2005, A2, . Location in patent: Page/Page column 527; 553; 554; 556
[10] Journal of Medicinal Chemistry, 2012, vol. 55, # 6, p. 2846 - 2857
[11] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 1902 - 1906
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 8, p. 3119 - 3126
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