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[ CAS No. 23945-44-0 ]

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Chemical Structure| 23945-44-0
Chemical Structure| 23945-44-0
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CAS No. :23945-44-0 MDL No. :MFCD00075737
Formula : C5H4N2O4 Boiling Point : 564.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :156.10 g/mol Pubchem ID :90301
Synonyms :

Safety of [ 23945-44-0 ]

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

Application In Synthesis of [ 23945-44-0 ]

  • Upstream synthesis route of [ 23945-44-0 ]
  • Downstream synthetic route of [ 23945-44-0 ]

[ 23945-44-0 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 65-71-4 ]
  • [ 4433-40-3 ]
  • [ 1195-08-0 ]
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Reference: [1] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038
  • 2
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YieldReaction ConditionsOperation in experiment
96.1% With dihydrogen peroxide; 1-hydroxy-1,2,3-benzotriazine-4(3H)-one In water at 130℃; for 3 h; Autoclave Add 100 g of thymine and 300 mL of water to the autoclave, and add 35 mL of hydrogen peroxide at a concentration of 30percent.15 g of 1-hydroxy-1,2,3-benzotriazine-4(3H)-one and 35 g of the catalyst prepared in Example 3, replacing the inside of the autoclave with an oxygen atmosphere, and heating to 130 ° C for 3 h.The reaction solution was cooled, filtered, concentrated, and placed in an ice-water mixture to cool.150 g of a white solid was precipitated, the yield was 96.1percent, and the purity was 99.3percent.
Reference: [1] Patent: CN108341785, 2018, A, . Location in patent: Paragraph 0014-0020
[2] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038
[3] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038
  • 3
  • [ 1195-08-0 ]
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Reference: [1] Canadian Journal of Chemistry, 2005, vol. 83, # 10, p. 1731 - 1740
[2] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038
  • 4
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Reference: [1] Canadian Journal of Chemistry, 2005, vol. 83, # 10, p. 1731 - 1740
  • 5
  • [ 110821-07-3 ]
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Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 2136,2140
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 11, p. 3181 - 3190
  • 7
  • [ 65-71-4 ]
  • [ 1195-08-0 ]
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Reference: [1] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038
  • 8
  • [ 4425-56-3 ]
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Reference: [1] Journal of the Chemical Society, 1955, p. 1834,1838
  • 9
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Reference: [1] Journal of the Chemical Society, 1955, p. 1834,1838
  • 10
  • [ 4433-40-3 ]
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Reference: [1] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038
  • 11
  • [ 65-71-4 ]
  • [ 4433-40-3 ]
  • [ 1195-08-0 ]
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Reference: [1] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038
  • 12
  • [ 3650-93-9 ]
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  • [ 71-30-7 ]
Reference: [1] Chemical Research in Toxicology, 1996, vol. 9, # 4, p. 745 - 750
  • 13
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  • [ 37131-89-8 ]
YieldReaction ConditionsOperation in experiment
65% With N,N-diethylaniline; trichlorophosphate In N,N-dimethyl-formamide at 90℃; for 2.66667 h; Under cold conditions To 10.0 g (64.06 mmol) of uracil-5-carboxylic acid (Aldrich Chemical Company) partially dissolved in 20 mL of DMF are added, under cold conditions, 59.7 mL (0.64 mol) of phosphorus oxychloride and 10.3 mL (64.7 mmol) of N,N-diethylaniline, and the mixture is then heated at 90° C. for 2 hours 40 minutes.
After cooling to room temperature and evaporating off half the excess POCl3, the medium is poured onto ice and then extracted with ether.
The ether phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum. 8.1 g (41.97 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid are obtained in a yield of 65percent.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 24, p. 6352 - 6356
[2] Patent: US2012/277220, 2012, A1, . Location in patent: Page/Page column 16
[3] Journal of Organic Chemistry, 1955, vol. 20, p. 829,833,835
[4] Patent: CN104650045, 2017, B, . Location in patent: Paragraph 0106; 0108
  • 14
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  • [ 51940-64-8 ]
Reference: [1] Patent: US2011/251194, 2011, A1,
  • 15
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  • [ 42821-92-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 1, p. 87 - 94
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 10, p. 1731 - 1740
  • 16
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  • [ 2972-52-3 ]
YieldReaction ConditionsOperation in experiment
100% at 0℃; for 16 h; Inert atmosphere; Reflux Example 9; 7-Amino-8-ethyl-5-oxo-2-[4-(3-pyridin-3-ylmethylureido)phenyl]-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid Methylamide (No. 53)9.1: 2,4-Dihydroxypyrimidine-5-carbonyl Chloride In a 250 ml round-bottomed flask, under a nitrogen atmosphere, 10.0 g (64.0 mmol) of 2,4-dihydroxypyrimidine-5-carboxylic acid are dissolved in 46 ml (500.0 mmol) of POCl3. The temperature of the mixture is reduced to 0° C. by means of an ice bath, and then 47.7 g (230 mmol) of PCl5 are added in small portions. The solution is stirred for 16 h at reflux and the solvents are then evaporated off under reduced pressure. The residue is taken up and triturated in 100 ml of toluene and then filtered. This operation is repeated three times and then the filtrate is evaporated under reduced pressure, so as to give 13.5 g (64.0 mmol) of compound in the form of a yellow oil which is used directly for the next stage. Yield=100percent.
99% at 0℃; for 16 h; Reflux 11.1: 2,4-Dichloropyrimidine-5-carbonyl chloride
2,4-Dihydroxypyrimidine-5-carboxylic acid (10 g, 64 mmol) is dispersed in POCl3 (45 ml) at 0° C. PCl5 (46.6 g, 224 mmol) is carefully added and the mixture is stirred under gentle reflux for 16 h.
The slightly yellow solution is evaporated under reduced pressure and the solid is washed with toluene, and the solution is filtered and the filtrate evaporated to give 13.4 g (yd: 99percent) of the compound. 1H NMR, d6-DMSO (300 MHz): 9.13 (s, 1H).
99% at 0℃; for 16 h; Reflux To POC13 (45mL, 0.07 1 mol) in a round bottom flask was added 2,4-dihydroxypyrimidine-5-carboxylic acid(10.00 g, 0.064 mol) portion wise at 0 °C, followed by slow addition of PC15 (46.60 g, 0.229 mol). The reaction mixture was warmed to r.t. and heated to reflux for 16 h. The mixture was concentrated to dryness, slurried with DCM (30 mL), and the solid precipitated was filtered and washed with DCM (2 x 20 mL). The filtrate was evaporated under reduced pressure to afford the title compound (13.900 g, 99percent) as a yellow oil. ‘H NMR (400 MHz, CDC13): ö 9.25 (s, 1H).
92% at 115℃; for 12 h; To a solution of 2,4-dihydroxypyrimidine-5- carboxylic acid (5.0 g, 32.0 mmol) in POCI3 (50 mL) was added PCI5 (23.9 g, 115.2 mmol), and the resulting solution was heated to 115 °C and stirred for 12 h. The solvent was evaporated and the crude residue was diluted with ethyl acetate (100 mL). The solid was filtered and the filtrate was concentrated to give the title compound as brown oil (6.2 g, 92percent).
4.38 g for 4.5 h; Reflux 5.1.32
2,4-Dichloropyrimidine-5-carboxamide (27)
To a solution of 2,4-dihydroxypyrimidine-5-carboxylic acid (25) (2.98 g, 19.1 mmol) in POCl3 (7.10 mL, 76.4 mmol) was added PCl5 (13.1 g, 63.0 mmol) and the reaction mixture was refluxed for 4.5 h.
After cooling, the reaction mixture was concentrated in vacuo.
To the resulting residue, toluene (20 mL) was added and the mixture was concentrated in vacuo again.
The residue was dissolved in CH2Cl2 (20 mL) and filtered.
The filtrate was concentrated in vacuo to give 2,4-dichloropyrimidine-5-carbonyl chloride (26) as a yellow oil (4.38 g).
This compound was used for next reaction without further purification. To a solution of 26 (4.38 g) in CH2Cl2 (5 mL) were added 28percent NH3 aqueous solution (3 mL) and H2O (3 mL) at -10 °C, and the reaction mixture was stirred at -10 °C for 5 min.
The organic solvent was removed under reduced pressure and the resulting precipitate was collected by filtration to give the title compound (3.13 g, 16.3 mmol, 85percent from 25) as a pale yellow solid. 1H NMR (DMSO-d6) δ: 8.05 (1H, s), 8.17 (1H, s), 8.90 (1H, s); MS (ESI) m/z: 192 (M+H)+.

Reference: [1] Patent: US2011/251194, 2011, A1, . Location in patent: Page/Page column 21
[2] Patent: US2010/222319, 2010, A1, . Location in patent: Page/Page column 18
[3] Patent: WO2015/21149, 2015, A1, . Location in patent: Page/Page column 56; 57
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2746 - 2763
[5] Patent: WO2015/48662, 2015, A2, . Location in patent: Page/Page column 55
[6] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 591 - 594
[7] Patent: US2003/216406, 2003, A1,
[8] Tetrahedron Letters, 2010, vol. 51, # 34, p. 4486 - 4489
[9] Patent: US5811428, 1998, A,
[10] Patent: US4734418, 1988, A,
[11] Patent: WO2005/9443, 2005, A1, . Location in patent: Page/Page column 75-76
[12] Patent: WO2010/97248, 2010, A1, . Location in patent: Page/Page column 31
[13] Patent: WO2007/24680, 2007, A1, . Location in patent: Page/Page column 42
[14] Patent: US2011/130415, 2011, A1, . Location in patent: Page/Page column 41
[15] Patent: US2012/22092, 2012, A1, . Location in patent: Page/Page column 29
[16] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 7025 - 7037
[17] Patent: WO2016/116563, 2016, A1, . Location in patent: Page/Page column 38-39
  • 17
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  • [ 2972-52-3 ]
YieldReaction ConditionsOperation in experiment
64% at 20 - 115℃; Procedure 6 - Preparation of 2,4-dichloro-pyrimidine-5-carbonyl chloride :; A mixture of 30,0 g (192 mmol) 5-carboxyuracil, 44,8 ml (480 mmol) phosphorus oxychloride and 132,0 g (634 mmol) phosphorus pentachloride is stirred under <n="214"/>argon for 6 hours at 115 0C. The mixture is then stirred overnight at room temperature. The mixture is filtered and the filter cake then washed with toluene. The filtrate is first concentrated on the rotary evaporator. The residue obtained is then purified by vacuum distillation (80-900C at 0,15 mbar). 26,0 g (123 mmol; corresponding to 64percent of theory) of the product is obtained.
64% at 115℃; for 6 h; A mixture of 30,0 g (192 mmol) 5-carboxyuracil, 44,8 ml (480 mmol) phosphorus oxychloride and 132,0 g (634 mmol) phosphorus pentachloride is stirred under argon for 6 hours at 115° C. The mixture is then stirred overnight at room temperature. The mixture is filtered and the filter cake then washed with toluene. The filtrate is first concentrated on the rotary evaporator. The residue obtained is then purified by vacuum distillation (80-90° C. at 0,15 mbar). 26,0 g (123 mmol; corresponding to 64percent of theory) of the product is obtained.
Reference: [1] Patent: WO2007/71455, 2007, A1, . Location in patent: Page/Page column 212-213
[2] Patent: US2007/232632, 2007, A1, . Location in patent: Page/Page column 87
[3] Patent: CN104650045, 2017, B,
  • 18
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  • [ 330784-47-9 ]
Reference: [1] Patent: CN104650045, 2017, B,
  • 19
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  • [ 1240390-28-6 ]
Reference: [1] Patent: WO2010/129802, 2010, A1, . Location in patent: Page/Page column 125
[2] Patent: US2011/130415, 2011, A1,
[3] Patent: US2012/22092, 2012, A1,
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 7025 - 7037
[5] Patent: WO2015/48662, 2015, A2,
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