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[ CAS No. 598-50-5 ] {[proInfo.proName]}

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Chemical Structure| 598-50-5
Chemical Structure| 598-50-5
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Product Details of [ 598-50-5 ]

CAS No. :598-50-5 MDL No. :MFCD00007950
Formula : C2H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :XGEGHDBEHXKFPX-UHFFFAOYSA-N
M.W : 74.08 Pubchem ID :11719
Synonyms :

Calculated chemistry of [ 598-50-5 ]

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 17.83
TPSA : 55.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.69
Log Po/w (XLOGP3) : -1.4
Log Po/w (WLOGP) : -0.72
Log Po/w (MLOGP) : -0.96
Log Po/w (SILICOS-IT) : -1.22
Consensus Log Po/w : -0.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.65
Solubility : 330.0 mg/ml ; 4.45 mol/l
Class : Highly soluble
Log S (Ali) : 0.74
Solubility : 411.0 mg/ml ; 5.55 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.23
Solubility : 124.0 mg/ml ; 1.68 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 598-50-5 ]

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

Application In Synthesis of [ 598-50-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 598-50-5 ]
  • Downstream synthetic route of [ 598-50-5 ]

[ 598-50-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 141-82-2 ]
  • [ 598-50-5 ]
  • [ 2565-47-1 ]
YieldReaction ConditionsOperation in experiment
65.8% With acetic anhydride In acetic acid at 90℃; To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70 °C, acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90 0C for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8percent). m.p. = 131.2-133.1 0C [Lit.1: m.p. = 130-131.5 0C].
65.8% With acetic anhydride In acetic acid at 70 - 90℃; for 3 h; (a) l-Methylpyrimidine-2,4,6(1H,3H,5H.)-trione To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70 0C, acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90 0C for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8percent). m.p. = 131.2-133.1 0C [Lit.1: m.p. = 130-131.5 0C].
65.8% With acetic anhydride In acetic acid at 70 - 90℃; for 3 h; To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70 0C, acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90 0C for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8percent). m.p. = 131.2-133.1 0C [Lit.1: m.p. = 130-131.5 0C].
64% at 70 - 90℃; for 3 h; To a solution of 1-methylurea (14 g, 189 mmol, 1.0 eq.) and malonic acid (23.6 g, 226.8 mmol, 1.2 eq.) in acetic acid (60 mL), acetic anhydride (36 mL, 378 mmol, 2.0 eq.) was added slowly at 70° C. After the completion of the addition, the reaction mixture was stirred at 90° C. for 3 h and then cooled to rt. The reaction mixture was concentrated and the residue was diluted with EtOH (100 mL). The solid was collected and re-crystalized in EtOH to give the title compound (17.0 g, 64percent yield) as a light yellow solid. LC-MS (ES, m/z): [M+H]+=143; 1H NMR (400 MHz, DMSO-d6): δ 11.32 (s, 1H), 3.58 (s, 2H), 2.50 (s, 3H) ppm.

Reference: [1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 3, p. 594 - 597
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 6, p. 1231 - 1237
[3] Patent: WO2009/73210, 2009, A1, . Location in patent: Page/Page column 76
[4] Patent: WO2006/133261, 2006, A2, . Location in patent: Page/Page column 30
[5] Patent: WO2007/143705, 2007, A2, . Location in patent: Page/Page column 23
[6] Patent: US2016/176868, 2016, A1, . Location in patent: Paragraph 0271; 0272
[7] Chemische Berichte, 1921, vol. 54, p. 1039
[8] Journal of the American Chemical Society, 1956, vol. 78, p. 6185,6187
[9] Chemical Communications, 2009, # 46, p. 7152 - 7154
[10] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 23, p. 6183 - 6193
  • 2
  • [ 105-53-3 ]
  • [ 598-50-5 ]
  • [ 2565-47-1 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With sodium In ethanol for 1 h;
Stage #2: for 24 h; Reflux
Methyl urea (97.14 g, 1.31 mol), absolute ethanol 1.2 L, metal sodium (30.4 g, 1.32 mol) was added in portions and stirred for 1 h. Diethyl malonate (273.0 g, 1.70 mol) in 100 mL of absolute ethanol was slowly added dropwise to the reaction solution, heating To reflux, reaction 24h. The solvent was evaporated under reduced pressure, 1 L of water was added, and the pH was adjusted to 3 to 4 with 2N HCl, followed by cooling and crystallization. Filter, wash, dry Drying gave a pale yellow powder, 152.8 g of 1-methylpyrimidine-2,4,6-trione, a yield of 82percent, mp. 129-130°C.
Reference: [1] Patent: CN107698560, 2018, A, . Location in patent: Paragraph 0029; 0030
[2] European Journal of Organic Chemistry, 2010, # 27, p. 5217 - 5224
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1987, vol. 23, # 6, p. 690 - 697[4] Khimiya Geterotsiklicheskikh Soedinenii, 1987, vol. 23, # 6, p. 836 - 844
[5] Chemistry of Natural Compounds, 2001, vol. 37, # 6, p. 543 - 550
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 5, p. 1105 - 1108
[7] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 2, p. 813 - 826
  • 3
  • [ 141-82-2 ]
  • [ 108-24-7 ]
  • [ 598-50-5 ]
  • [ 2565-47-1 ]
  • [ 89694-18-8 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 6185,6187
  • 4
  • [ 105-56-6 ]
  • [ 598-50-5 ]
  • [ 2434-53-9 ]
YieldReaction ConditionsOperation in experiment
63% With sodium In ethanolReflux General procedure: Compounds 1a, 1b and 1e were prepared according to the reportedmethods26–34 by the addition of urea, methylurea and/or methylthiourea (0.1 mol) to ethyl cyanoacetate (0.1 mol) in absolute ethanol(290 mL) containing sodium (0.2 mol). The mixture was refluxed for10–12 h, allowed to cool to r.t. and acidified with acetic acid (pH 6).The resulting precipitate was washed with distilled water and dried in adesiccator overnight.
32%
Stage #1: at 25℃; for 0.5 h; Reflux
Stage #2: for 3 h; Reflux
Sodium (7.80 g, 340 mmol) was added in batches to ethanol (180 mL) while stirring at 25 °C, heated to 80°C to reflux for 0.5 hours.
Methylurea (12.6 g, 170 mmol) was then added in batches and reflux was continued for 0.5 h.
Ethyl cyanoacetate (19.0 g, 170 mmol) was added dropwise to the reaction solution, resulting in a large amount of precipitate.
Reflux was continued for 3 hours, ethanol was recovered under reduced pressure.
The residue was diluted with water (50 mL) and adjusted to pH = 7 with dilute hydrochloric acid (1 N).
The product was filtered to give 6-amino-1-methylpyrimidine-2,4-dione (7.60 g, as a white solid) with a yield of 32percent. 1H NMR: (400 MHz, DMSO-d6) δ 10.39(br, 1H), 6.79(br, 2H), 4.54(s, 1H), 3.14(s, 3H). MS-ESI calcd. [M + H]+ 142, found 142.
32%
Stage #1: With sodium In ethanol at 25℃; for 0.5 h; Reflux
Stage #2: for 3 h; Reflux
At 25° C., metallic sodium (7.80 g, 340 mmol) was added into anhydrous ethanol (180 mL) in batches while stirring, followed by heating to 80° C. and refluxing for 0.5 hour.
Methylurea (12.6 g, 170 mmol) was then added in batches, and refluxing was continued for 0.5 hour.
Ethyl cyanoacetate (19.0 g, 170 mmol) was added into the reaction solution dropwise, and a large amount of precipitate was produced.
Refluxing was continued for 3 hours, and then ethanol was recovered under reduced pressure.
The residue was dissolved in water (50 mL), and the pH value was adjusted to pH=7 with diluted hydrochloric acid (1N), followed by filtration to give 6-amino-1-methylpyrimidin-2,4-dione (7.60 g, white solid) with a yield of 32percent. 1H NMR: (400 MHz, DMSO-d6) δ10.39 (s, 1H), 6.79 (s, 2H), 4.54 (s, 1H), 3.14 (s, 3H). MS-ESI calculated value: [M+H]+ 142; measured value: 142.
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 13, p. 2344 - 2350
[2] RSC Advances, 2015, vol. 5, # 28, p. 21464 - 21470
[3] Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 4, p. 477 - 482
[4] Journal of Chemical Research, 2016, vol. 40, # 12, p. 771 - 777
[5] Patent: EP3299371, 2018, A1, . Location in patent: Paragraph 0587; 0588
[6] Patent: US2018/148451, 2018, A1, . Location in patent: Paragraph 0331; 0332
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 1140
[8] Justus Liebigs Annalen der Chemie, 1905, vol. 340, p. 312
[9] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1397 - 1401
[10] Journal of Medicinal Chemistry, 2008, vol. 51, # 7, p. 2267 - 2278
[11] Journal of Combinatorial Chemistry, 2010, vol. 12, # 4, p. 510 - 517
[12] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 1139
  • 5
  • [ 372-09-8 ]
  • [ 598-50-5 ]
  • [ 2434-53-9 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 34, p. 5727 - 5729
[2] Journal of Organic Chemistry, 1951, vol. 16, p. 1879,1881,1887
[3] European Journal of Medicinal Chemistry, 1990, vol. 25, # 8, p. 653 - 658
[4] Arzneimittel-Forschung/Drug Research, 2010, vol. 60, # 3, p. 131 - 136
  • 6
  • [ 105-34-0 ]
  • [ 598-50-5 ]
  • [ 2434-53-9 ]
Reference: [1] Chemicke Zvesti, 1952, vol. 6, p. 357[2] Chem.Abstr., 1954, p. 7019
  • 7
  • [ 372-09-8 ]
  • [ 598-50-5 ]
  • [ 2434-53-9 ]
  • [ 21236-97-5 ]
Reference: [1] Meditsinskaya Promyshlennost SSSR, 1958, vol. 12, # 9, p. 16,20[2] Chem.Abstr., 1959, p. 16146
  • 8
  • [ 96-31-1 ]
  • [ 598-50-5 ]
  • [ 2434-53-9 ]
Reference: [1] Journal of Molecular Structure, 1997, vol. 435, # 2, p. 133 - 141
  • 9
  • [ 372-09-8 ]
  • [ 598-50-5 ]
  • [ 2434-53-9 ]
  • [ 21236-97-5 ]
Reference: [1] Meditsinskaya Promyshlennost SSSR, 1958, vol. 12, # 9, p. 16,20[2] Chem.Abstr., 1959, p. 16146
  • 10
  • [ 141-82-2 ]
  • [ 598-50-5 ]
  • [ 4318-56-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 18, p. 8685 - 8696
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