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Chemical Structure| 873-83-6
Chemical Structure| 873-83-6
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Product Details of [ 873-83-6 ]

CAS No. :873-83-6 MDL No. :MFCD00006071
Formula : C4H5N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LNDZXOWGUAIUBG-UHFFFAOYSA-N
M.W : 127.10 Pubchem ID :70120
Synonyms :

Calculated chemistry of [ 873-83-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 3.0
Molar Refractivity : 32.09
TPSA : 91.74 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) : -8.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.11
Log Po/w (XLOGP3) : -1.62
Log Po/w (WLOGP) : -1.35
Log Po/w (MLOGP) : -1.36
Log Po/w (SILICOS-IT) : 0.64
Consensus Log Po/w : -0.71

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.1
Solubility : 101.0 mg/ml ; 0.793 mol/l
Class : Very soluble
Log S (Ali) : 0.2
Solubility : 203.0 mg/ml ; 1.6 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.07
Solubility : 10.9 mg/ml ; 0.0857 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 873-83-6 ]

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

Application In Synthesis of [ 873-83-6 ]

* 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 [ 873-83-6 ]
  • Downstream synthetic route of [ 873-83-6 ]

[ 873-83-6 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 873-83-6 ]
  • [ 10132-07-7 ]
Reference: [1] Molecules, 2012, vol. 17, # 4, p. 4533 - 4544
  • 2
  • [ 873-83-6 ]
  • [ 91-66-7 ]
  • [ 10132-07-7 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 829,833,835
  • 3
  • [ 105-56-6 ]
  • [ 57-13-6 ]
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YieldReaction ConditionsOperation in experiment
69% 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.1a: Yield 69percent; m.p. > 360 °C (lit. ≥ 360 °C).
Reference: [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 7, p. 1053 - 1055
[2] Journal of Chemical Research, 2016, vol. 40, # 12, p. 771 - 777
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 7, p. 662 - 668
[4] Australian Journal of Chemistry, 2007, vol. 60, # 2, p. 120 - 123
[5] Oriental Journal of Chemistry, 2010, vol. 26, # 4, p. 1281 - 1292
[6] Justus Liebigs Annalen der Chemie, 1905, vol. 340, p. 312
[7] Chemische Berichte, 1936, vol. 69, p. 1621,1625
[8] Nippon Shashin Gakkaishi, 1950, vol. 13, p. 103,107[9] Chem.Abstr., 1952, p. 3885
[10] Org.Synth.Coll.Vol.IV<1963>247,
[11] Recueil des Travaux Chimiques des Pays-Bas, 1946, vol. 65, p. 751,764
[12] Patent: US2121811, 1937, ,
[13] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1946, vol. 19, p. 1340[14] Chem.Abstr., 1948, p. 1207
[15] Proceedings - Indian Academy of Sciences, Section A, 1953, vol. 37, p. 652,656,658
[16] Journal of Combinatorial Chemistry, 2010, vol. 12, # 4, p. 510 - 517
[17] Molecules, 2018, vol. 23, # 9,
[18] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 1139
[19] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 1141
[20] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 1080
  • 4
  • [ 372-09-8 ]
  • [ 57-13-6 ]
  • [ 873-83-6 ]
YieldReaction ConditionsOperation in experiment
78% With acetic anhydride; sodium hydroxide In neat (no solvent) for 0.166667 h; Microwave irradiation We have found that the microwave assisted of reaction urea (1 mmol) with cyano acetic acid (1 mmol) under solvent-free conditions results in rapid formation of the corresponding Amino uracil (Figure1).The products were easily obtained by addition of water to the reaction mixture and recrystalization of crude products from ethanol.
Reference: [1] Oriental Journal of Chemistry, 2014, vol. 30, # 3, p. 1379 - 1383
[2] Journal of Organic Chemistry, 1951, vol. 16, p. 1879,1881,1887
  • 5
  • [ 584-08-7 ]
  • [ 105-56-6 ]
  • [ 873-83-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1167 - 1172
  • 6
  • [ 1560-54-9 ]
  • [ 873-83-6 ]
  • [ 65996-50-1 ]
Reference: [1] Heteroatom Chemistry, 2002, vol. 13, # 4, p. 357 - 365
  • 7
  • [ 1448-98-2 ]
  • [ 873-83-6 ]
Reference: [1] Chemische Berichte, 1900, vol. 33, p. 1381,3044[2] Chem. Zentralbl., 1901, vol. 72, # I, p. 547
[3] Journal of the Chemical Society, 1909, vol. 95, p. 981
[4] Chemische Berichte, 1937, vol. 70, p. 761,765
[5] Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1970,1972;engl.Ausg.S.2012,2014
[6] Journal of the American Pharmaceutical Association (1912-1977), 1948, vol. 37, p. 62
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1189
  • 8
  • [ 1004-40-6 ]
  • [ 873-83-6 ]
Reference: [1] Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 3075 - 3077
  • 9
  • [ 591-07-1 ]
  • [ 105-56-6 ]
  • [ 873-83-6 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 1142
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 1143
  • 10
  • [ 52386-29-5 ]
  • [ 873-83-6 ]
  • [ 130056-78-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 4, p. 1079 - 1083
  • 11
  • [ 69-93-2 ]
  • [ 873-83-6 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2008, vol. 27, # 8, p. 967 - 978
  • 12
  • [ 52386-29-5 ]
  • [ 79-04-9 ]
  • [ 873-83-6 ]
  • [ 130056-78-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 4, p. 1079 - 1083
  • 13
  • [ 4270-27-3 ]
  • [ 873-83-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 6868 - 6877
  • 14
  • [ 873-83-6 ]
  • [ 67-52-7 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 20, p. 10402 - 10411
[2] RSC Advances, 2014, vol. 4, # 61, p. 32207 - 32213
  • 15
  • [ 873-83-6 ]
  • [ 100-52-7 ]
  • [ 67-52-7 ]
  • [ 27402-47-7 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 20, p. 10402 - 10411
  • 16
  • [ 7647-01-0 ]
  • [ 873-83-6 ]
  • [ 67-52-7 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1905, vol. 340, p. 312
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 7, p. 661
  • 17
  • [ 873-83-6 ]
  • [ 7664-93-9 ]
  • [ 67-52-7 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1905, vol. 340, p. 312
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 7, p. 661
  • 18
  • [ 873-83-6 ]
  • [ 80-48-8 ]
  • [ 2434-53-9 ]
Reference: [1] Yakugaku Zasshi, 1954, vol. 74, p. 674,676,678,681[2] Chem.Abstr., 1954, p. 10743
  • 19
  • [ 873-83-6 ]
  • [ 77-78-1 ]
  • [ 2434-53-9 ]
Reference: [1] Yakugaku Zasshi, 1954, vol. 74, p. 674,676,678,681[2] Chem.Abstr., 1954, p. 10743
  • 20
  • [ 873-83-6 ]
  • [ 74-88-4 ]
  • [ 21236-97-5 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: for 3 h; Reflux
Stage #2: at 20℃; for 72 h;
6-Aminouracil (5) (5.18 g, 40.7 mmol) was suspended in HM DS (25 mL) and H2S04 (0.1 m L) was added. The mixture was heated at reflux for 3 h then concentrated in vacuo. The residue was dissolved in DM F (30 mL), Mel (8.5 mL, 136.5 mmol) was added, and stirring was continued for 72 h at room temperature. The reaction was cooled to 0 °C and NaHC03 was carefully added. The mixture was stirred at 0 °C until no more bubbling was observed. The precipitate was filtered, washed with MeOH and H20 and dried to give the title compound 6 (4.49 g, 78percent) as a yellow solid which was used without further purification.Rf 0.23 (EtOAc-MeOH-N H4OH, 7:2.7:0.3);H NMR (400 MHz, DMSO-d6) δ 10.36 (1H, s, Ntf), 6.16 (2H, s, Ntf2), 4.56 (1H, s, tf-5); 3.04 (3H, s, NCtf3); 13C NMR (100 M Hz, DMSO-d6) δ 163.3 (C-4), 153.5 (C-6), 151.1 (C-2), 74.0 (C-5), 25.9 (NCH3);MP Lit: 327 °C19, found: 320-323 °C;
42.6%
Stage #1: for 6 h; Reflux
Stage #2: at 40℃; for 16 h;
Step 1 6-amino-3-methylpyrimidine-2,4(lH,3H)-dione To a solution of the 6-aminopyrimidine-2,4(lH,3H)-dione (15 g, 1 18 mmol) in 1 ,1 ,1 ,3,3,3- hexamethyldisilazane (50 mL) was added ammonium sulfate(0.671g, 5 mmol), then the resulting mixture was heated to reflux with stirring for 6 h. The mixture was concentrated to give a light-yellow solid. This solid was combined with acetonitrile (50 mL) and iodomethane (15 mL, 250 mmol) was added. The resulting mixture was stirred at 40 °C for 16 h. Then the mixture was concentrated, neutralized with saturated sodium bicarbonate to pH =7, filtered, and the filter cake was washed with brine and ethanol, dried under vacuum to give 6-amino-3- methylpyrimidine-2,4 (lH,3H)-dione (7.1 g, 42.6 percent yield) as yellow solid. LCMS MH+ 142.
Reference: [1] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 5079 - 5084
[2] Patent: WO2017/99612, 2017, A1, . Location in patent: Page/Page column 8; 28
[3] Patent: WO2014/143799, 2014, A2, . Location in patent: Page/Page column 372
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 5, p. 2001 - 2009
  • 21
  • [ 873-83-6 ]
  • [ 74-88-4 ]
  • [ 6642-31-5 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With potassium hydroxide In ethanol for 0.666667 h; Heating
Stage #2: for 8 h; Heating
To a heated ethanolic KOH solution (0.56 g, 10 mmol in 50 ml ethanol) compound 1 (1.27 g, 10 mmol) was added and heating was continuous for 40 min. The mixture was allowed to cool to room temperature, and methyl iodide (20 mmol) was added. The mixture was stirred under heating for 8 h and then allowed to cool to room temperature and finally poured into cold H2O (100 ml), The final product ppt. was filtered and washed with 100 ml H2O and crystallized from methanol to afford 2 as yellow crystals.
Reference: [1] Letters in Drug Design and Discovery, 2015, vol. 12, # 6, p. 471 - 478
[2] DRP/DRBP Org.Chem.,
[3] Patent: CN104744471, 2016, B, . Location in patent: Paragraph 0026; 0027; 0028
  • 22
  • [ 873-83-6 ]
  • [ 77-78-1 ]
  • [ 6642-31-5 ]
Reference: [1] DRP/DRBP Org.Chem.,
[2] Journal of the American Pharmaceutical Association (1912-1977), 1948, vol. 37, p. 62
[3] Patent: CN104744468, 2016, B, . Location in patent: Paragraph 0029
  • 23
  • [ 873-83-6 ]
  • [ 3346-22-3 ]
Reference: [1] Helvetica Chimica Acta, 1951, vol. 34, p. 835,837
  • 24
  • [ 1560-54-9 ]
  • [ 873-83-6 ]
  • [ 65996-50-1 ]
Reference: [1] Heteroatom Chemistry, 2002, vol. 13, # 4, p. 357 - 365
  • 25
  • [ 107-20-0 ]
  • [ 873-83-6 ]
  • [ 39929-79-8 ]
YieldReaction ConditionsOperation in experiment
80% With sodium acetate In water at 72 - 80℃; for 1 h; To a suspended solution of 6-aminouracil (32, 6.35 g, 50.0 mmol) and sodium acetate (4.10 g, 50.0 mmol) in H20 (50 mL) at a temperature of 72 °C was added a solution of chloroacetaldehyde (50percent in water, 11.8 g, 75.2 mmol) drop-wise. The reaction mixture was heated to 80 °C and stirring was continued for 60 mm. After cooling the reaction mixture to room temperature, the resulting solid was collected by filtration, washed with water and acetone, and dried under vacuum to afford 33 as a light-brown solid (6.46 g, 86percent). ‘H-NMR (400 MHz, DMSO-d6) ö 11.45 (s, 1H), 11.10 (s, 1H), 10.48 (s, 1H), 6.64-6.51 (m, 1H), 6.22 (t, J = 2.5 Hz, 1H); MS (m/z) [M+Hj 152.06.
33% With sodium acetate In water for 3 h; Heating / reflux A solution of commercially available 6-amino-1 H-pyrimidine-2,4-dione (25 g, 0.2 mol) and NaOAc (20 g, 0.24 mol) in 1.25 L of distilled water was treated with chloroacetaldehyde (25 ml_, 50percent w/w in water). After 3 h at reflux, the reaction mixture was filtered while still warm, to remove the brown solid. The yellow mother liquor was cooled to RT then acidified to pH ~ 4 by addition of 2.5 M HCI. The desired product (9.722 g, 33percent) was isolated by filtration and finally dried in the oven. 1H NMR (cfe-DMSO) δ 11.46 (1 H, br s), 11.11 (1 H, br s), 10.49 (1 H, br s), 6.57 (1 H, dd, J = 2.0, 3.6 Hz), 6.22 (1 H, dd, J = 2.0, 3.2 Hz).
Reference: [1] Tetrahedron, 2014, vol. 70, # 33, p. 4947 - 4956
[2] Patent: WO2018/137036, 2018, A1, . Location in patent: Paragraph 00233; 00234
[3] Synlett, 2005, # 5, p. 744 - 750
[4] Patent: WO2009/37467, 2009, A1, . Location in patent: Page/Page column 15-16; 13
  • 26
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Reference: [1] European Journal of Medicinal Chemistry, 2008, vol. 43, # 6, p. 1248 - 1260
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