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[ CAS No. 22325-27-5 ] {[proInfo.proName]}

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Chemical Structure| 22325-27-5
Chemical Structure| 22325-27-5
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Product Details of [ 22325-27-5 ]

CAS No. :22325-27-5 MDL No. :MFCD00006079
Formula : C6H8N2S Boiling Point : -
Linear Structure Formula :- InChI Key :RAFAYWADRVMWFA-UHFFFAOYSA-N
M.W : 140.21 Pubchem ID :673664
Synonyms :

Calculated chemistry of [ 22325-27-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.35
TPSA : 60.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 0.57
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 0.18
Log Po/w (SILICOS-IT) : 3.38
Consensus Log Po/w : 1.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.56
Solubility : 3.85 mg/ml ; 0.0274 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 5.34 mg/ml ; 0.0381 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.433 mg/ml ; 0.00309 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 22325-27-5 ]

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

Application In Synthesis of [ 22325-27-5 ]

* 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 [ 22325-27-5 ]
  • Downstream synthetic route of [ 22325-27-5 ]

[ 22325-27-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 100-46-9 ]
  • [ 22325-27-5 ]
  • [ 4472-44-0 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 3, p. 1080 - 1084
  • 2
  • [ 22325-27-5 ]
  • [ 23906-13-0 ]
Reference: [1] Bollettino chimico farmaceutico, 2004, vol. 143, # 7, p. 275 - 279
  • 3
  • [ 17356-08-0 ]
  • [ 123-54-6 ]
  • [ 22325-27-5 ]
YieldReaction ConditionsOperation in experiment
80.22% for 2 h; 5 - ((4,6-dimethyl-pyrimidin-2 -) sulfur methyl) - 1, 3, 4-oxadiazol-2-thiol can reference the literature (Tetrahedron., 2005,61 (23): 5565) synthetic method: the thiourea (19g, 0.25mol), acetyl acetone (25.8 ml, 0 . 25mol), 125 ml of ethanol, into a reaction flask, water bath reflow 2h, slightly cooling, funnel instillment for 33.5 ml of concentrated hydrochloric acid, to continue to reflow heating, to get the yellow crystal filtering, desolvation, heating solution, dissolved with a 10percent NaOH solution to adjust the pH≈ 7 of, is cooling at room temperature, to be 4,6-dimethyl pyrimidine-2-thiol: pale yellow needle crystal, yield 80.22percent, melting point 209-211° C (for fire 210 °C).
80.22%
Stage #1: for 2 h; Reflux
Stage #2: With hydrogenchloride In water for 1 h; Reflux
19 g thiourea (0.25 mol), 25.8 mL of acetylacetone (0.25 mol) and 125 mL of ethanol. The reaction mixture was refluxed for 2 h in a water bath, and 33.5 mL of concentrated hydrochloric acid was added dropwise. The mixture was refluxed for 1 h. A small yellow crystal precipitation, filtration, desolvation, the crystal with 40 mL of water heating dissolved with 10percent NaOH solution to adjust the pH ≈ 7, a large number of pale yellow needle crystal precipitation, filtration, washing, vacuum drying the target product 1 (4,6-dimethylpyrimidine-2-thiol). Yield 80.22percent, melting point 209 ~ 211.
10.75 mL of ethyl chloroacetate (0.086 mol) and 11.8 g of potassium carbonate (0.086 mol) as the acid binding agent in 100 mL of acetone were used as the eluent. Heating reflux reaction, TLC detection reaction process, until the reaction is completed, cooled to room temperature, filter to remove inorganic matter, remove the solvent under reduced pressure, was light yellow thick liquid. Washed and extracted to give the target product 2 (ethyl 2 - ((4,6-dimethylpyrimidin-2-yl) thio) acetate. Yield 95percent.
The ethyl 2 - ((4,6-dimethylpyrimidin-2-yl) thio) acetate obtained in the previous step was dissolved in absolute ethanol and 10.5 g of 85percent hydrazine hydrate (0.213 mol) was added. The reaction mixture was heated to reflux and the reaction progressed by TLC. After the reaction was completed, the reaction mixture was cooled to room temperature and a large amount of white solid was removed by removing the solvent under reduced pressure. The crude product was obtained by washing, suction filtration and drying. ). Yield 92percent.
80.22%
Stage #1: for 2 h; Reflux
Stage #2: With hydrogenchloride In ethanol; water for 1 h; Reflux
4,6-dimethyl pyrimidine-2-thiol reference literature (Aust.J.Chem., 2007,60:120) method to synthesize: the thiourea (19g, 0.25mol), acetyl acetone (25.8 ml, 0 . 25mol), 125 ml of ethanol, the solution is colorless, water bath heating reflux 2h, after slightly cooling, dropping funnel for dropping 33.5 ml of concentrated hydrochloric acid, to continue heating reflux 1h, TLC detection reaction end, placing sleepovers. With yellow tiny crystal precipitation, filtration, desolvation, for of the crystal 40 ml water heating is dissolved, is dissolved with a 10percent NaOH solution to adjust the pH≈ 7 of, is cooling at room temperature, filtered, washing with water, dried under vacuum to get the 4,6-dimethyl pyrimidine-2-thiol: pale yellow needle crystal, yield 80.22percent.
Reference: [1] Bollettino chimico farmaceutico, 2004, vol. 143, # 7, p. 275 - 279
[2] Patent: CN105585538, 2016, A, . Location in patent: Paragraph 0024
[3] Patent: CN105859693, 2016, A, . Location in patent: Paragraph 0021
[4] Patent: CN105622599, 2016, A, . Location in patent: Paragraph 0022
[5] Zeitschrift fur Anorganische und Allgemeine Chemie, 2015, vol. 641, # 7, p. 1301 - 1306
[6] Journal of the Indian Chemical Society, 1983, vol. 60, # 6, p. 583 - 584
[7] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1599 - 1612
[8] Acta Crystallographica Section C: Crystal Structure Communications, 2013, vol. 69, # 4, p. 384 - 387
  • 4
  • [ 5663-07-0 ]
  • [ 123-54-6 ]
  • [ 22325-27-5 ]
Reference: [1] Chemistry - An Asian Journal, 2009, vol. 4, # 5, p. 668 - 680
  • 5
  • [ 41041-25-2 ]
  • [ 22325-27-5 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1980, vol. 29, p. 1820 - 1823[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1980, # 11, p. 2564 - 2568
  • 6
  • [ 62501-45-5 ]
  • [ 22325-27-5 ]
Reference: [1] Asian Journal of Chemistry, 2015, vol. 27, # 1, p. 287 - 291
  • 7
  • [ 39994-75-7 ]
  • [ 41840-28-2 ]
  • [ 60538-19-4 ]
  • [ 22325-27-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 4, p. 1342 - 1350
  • 8
  • [ 4472-44-0 ]
  • [ 64-17-5 ]
  • [ 22325-27-5 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3956
  • 9
  • [ 7647-01-0 ]
  • [ 64-17-5 ]
  • [ 17356-08-0 ]
  • [ 123-54-6 ]
  • [ 22325-27-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 508[2] Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 46, p. 352
  • 10
  • [ 22325-27-5 ]
  • [ 35144-22-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 11, p. 2776 - 2795
[2] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2288 - 2300
  • 11
  • [ 78-83-1 ]
  • [ 102-13-6 ]
  • [ 22325-27-5 ]
Reference: [1] Asian Journal of Chemistry, 2015, vol. 27, # 1, p. 287 - 291
  • 12
  • [ 100-01-6 ]
  • [ 4850-93-5 ]
  • [ 22325-27-5 ]
Reference: [1] Asian Journal of Chemistry, 2015, vol. 27, # 1, p. 287 - 291
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