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[ CAS No. 16632-21-6 ] {[proInfo.proName]}

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Chemical Structure| 16632-21-6
Chemical Structure| 16632-21-6
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Product Details of [ 16632-21-6 ]

CAS No. :16632-21-6 MDL No. :MFCD00047362
Formula : C5H5N3O4 Boiling Point : -
Linear Structure Formula :- InChI Key :LIVYMRJSNFHYEN-UHFFFAOYSA-N
M.W : 171.11 Pubchem ID :85523
Synonyms :
5-Nitro-6-methyluracil

Calculated chemistry of [ 16632-21-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.47
TPSA : 111.54 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) : -7.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.1
Log Po/w (XLOGP3) : -0.56
Log Po/w (WLOGP) : -0.72
Log Po/w (MLOGP) : -1.77
Log Po/w (SILICOS-IT) : -0.4
Consensus Log Po/w : -0.67

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.85
Solubility : 24.1 mg/ml ; 0.141 mol/l
Class : Very soluble
Log S (Ali) : -1.31
Solubility : 8.33 mg/ml ; 0.0487 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.23
Solubility : 10.1 mg/ml ; 0.0589 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 16632-21-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16632-21-6 ]

* 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 [ 16632-21-6 ]
  • Downstream synthetic route of [ 16632-21-6 ]

[ 16632-21-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 16632-21-6 ]
  • [ 20090-69-1 ]
Reference: [1] Patent: CN105906621, 2016, A,
  • 2
  • [ 16632-21-6 ]
  • [ 6270-46-8 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 2418,2422
  • 3
  • [ 16632-21-6 ]
  • [ 13162-27-1 ]
Reference: [1] Patent: CN105906621, 2016, A,
  • 4
  • [ 626-48-2 ]
  • [ 16632-21-6 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: at 0 - 40℃;
Stage #2: at 15 - 20℃; for 0.5 h;
The procedure was adapted from that reported in J. Med. Chem. 1976, 19, 1072. 6-Methylpyrimidine-2,4(lH,3H)-dione (7.Og, 55.56mmol) was added to concentrated sulfuric acid (26 mL) cooled in ice at such a rate that the internal <n="99"/>temperature did not exceed 40°. To this mixture fuming nitric acid (5.2 mL) was added dropwise whilst maintaining the temperature below 15°. The cooling bath was removed and the mixture was stirred at room temperature for 30 min then dumped into 100ml of crushed ice. After stirring for 10 min the solid was collected and washed with cold water then dried in vacuo over phosphorus pentoxide. A yellow-green solid of 6- rnethyl-5-nitropyrimidine-2,4(lH,3H)-dione was obtained (7.92 g, 83percent).
65.2% at -2 - 35℃; for 12 h; The raw material 11 (6.3g) was dissolved in 30ml concentrated sulfuric acid and slowly mixed with low acid (concentrated sulfuric acid / concentrated nitric acid = 10ml / 12ml) at -2 . Finally, the reaction was carried out at 35 for 12h.The reaction solution was poured into ice water and precipitated with a large amount of a pale yellow solid. After filtration under reduced pressure, a pale yellow solid 12 (4 g) was obtained in a yield of 65.2percent.
2.7 g at 50℃; for 10 h; Inert atmosphere To a stirred mixture of 96percent H2S04(15 mL) and of 70percent HN03(15 mL) was added 6- methyl pyrimidine-2,4-(lH,3H)-dione (2.5 g,19.8 mmol). The solution was kept at 50 °C for lOh. The mixture was cooled to room temperature and poured into a large volume of ice water. The solid was collected and dried in vacuo. Recrystallization with MeOH gave the final compound (2.7g,16.2 mmol) as yellows solid.1H NMR (200 MHz,DMSO) δ 2.31 (s,3H), 11.82 (s,1H), 11.85 (s,1H).
Reference: [1] Journal of Chemical Research, Miniprint, 1989, # 9, p. 2086 - 2097
[2] Patent: WO2009/62258, 2009, A1, . Location in patent: Page/Page column 97-98
[3] Synthetic Communications, 2007, vol. 37, # 14, p. 2421 - 2431
[4] ChemMedChem, 2018, vol. 13, # 2, p. 178 - 185
[5] Patent: CN105906621, 2016, A, . Location in patent: Paragraph 0030
[6] Chemische Berichte, 1901, vol. 34, p. 1242
[7] Justus Liebigs Annalen der Chemie, 1887, vol. 240, p. 11
[8] Justus Liebigs Annalen der Chemie, 1905, vol. 343, p. 138
[9] Patent: US6002004, 1999, A,
[10] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 205 - 212
[11] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 7, p. 1749 - 1755
[12] Chemical Biology and Drug Design, 2015, vol. 85, # 3, p. 296 - 299
[13] Patent: CN106866678, 2017, A, . Location in patent: Paragraph 0114; 0116; 0117; 0118; 0119; 0120
[14] Patent: WO2018/69532, 2018, A1, . Location in patent: Paragraph 0547; 0549
  • 5
  • [ 116705-41-0 ]
  • [ 16632-21-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 985 - 990
  • 6
  • [ 16632-21-6 ]
  • [ 13162-26-0 ]
YieldReaction ConditionsOperation in experiment
65% With <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate In N,N-dimethyl-formamide at 120℃; for 8 h; The raw material 12 (1 eq) was dissolved in 17.54 ml of phosphorus oxychloride, and 2.92 ml of N, N-dimethylaniline (1 eq) was slowly added dropwise at room temperature, and 8.04 ul of DMF (0.00445 eq) 120 under reflux reaction 8h, after the completion of the reaction of raw materials, vacuum distillation of phosphorus oxychloride, adding ice water, adding ethyl acetate extraction, combined organic layer, washed with saturated brine, dried over anhydrous sodium sulfate, spin dry Solvent to give a yellowish brown oil which was dryly chromatographed and finally purified to give a yellow solid 13 (1 g) in 65percent yield.
Reference: [1] Patent: CN105906621, 2016, A, . Location in patent: Paragraph 0031
[2] Bulletin de la Societe Chimique de France, 1951, p. 428
[3] Helvetica Chimica Acta, 1951, vol. 34, p. 835,837
[4] Journal of the Chemical Society, 1951, p. 1004,1015[5] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, vol. 24, p. 84
[6] Journal of the Chemical Society, 1955, p. 1113,1115
[7] Journal of the Chemical Society, 1954, p. 3832,3833
[8] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5723 - 5730
[9] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5723 - 5730
  • 7
  • [ 16632-21-6 ]
  • [ 13162-26-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4879 - 4883
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2188 - 2192
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 15, p. 2497 - 2500
[4] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 6, p. 1395 - 1399
  • 8
  • [ 16632-21-6 ]
  • [ 121-69-7 ]
  • [ 13162-26-0 ]
  • [ 7460-27-7 ]
Reference: [1] Journal of the Chemical Society, 1951, p. 1004,1015[2] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, vol. 24, p. 84
  • 9
  • [ 16632-21-6 ]
  • [ 10025-87-3 ]
  • [ 13162-26-0 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 1242
  • 10
  • [ 16632-21-6 ]
  • [ 54368-61-5 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1989, # 9, p. 2086 - 2097
  • 11
  • [ 16632-21-6 ]
  • [ 65996-50-1 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1988, vol. 22, # 2, p. 135 - 141[2] Khimiko-Farmatsevticheskii Zhurnal, 1988, vol. 22, # 2, p. 185 - 191
[3] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 205 - 212
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 7, p. 1749 - 1755
[5] Patent: CN106866678, 2017, A,
[6] ChemMedChem, 2018, vol. 13, # 2, p. 178 - 185
  • 12
  • [ 16632-21-6 ]
  • [ 63200-54-4 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1988, vol. 22, # 2, p. 135 - 141[2] Khimiko-Farmatsevticheskii Zhurnal, 1988, vol. 22, # 2, p. 185 - 191
[3] Pharmaceutical Chemistry Journal, 1988, vol. 22, # 2, p. 135 - 141[4] Khimiko-Farmatsevticheskii Zhurnal, 1988, vol. 22, # 2, p. 185 - 191
[5] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 205 - 212
[6] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 7, p. 1749 - 1755
[7] Patent: CN106866678, 2017, A,
[8] ChemMedChem, 2018, vol. 13, # 2, p. 178 - 185
  • 13
  • [ 16632-21-6 ]
  • [ 633328-98-0 ]
Reference: [1] Patent: CN105906621, 2016, A,
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