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[ CAS No. 4765-77-9 ] {[proInfo.proName]}

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Chemical Structure| 4765-77-9
Chemical Structure| 4765-77-9
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Product Details of [ 4765-77-9 ]

CAS No. :4765-77-9 MDL No. :MFCD00233957
Formula : C4H3ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :AXFABVAPHSWFMD-UHFFFAOYSA-N
M.W :130.53 Pubchem ID :135445478
Synonyms :

Calculated chemistry of [ 4765-77-9 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.87
TPSA : 45.75 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) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.0
Log Po/w (XLOGP3) : 0.13
Log Po/w (WLOGP) : 0.42
Log Po/w (MLOGP) : -0.4
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 0.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.29
Solubility : 6.75 mg/ml ; 0.0517 mol/l
Class : Very soluble
Log S (Ali) : -0.65
Solubility : 29.4 mg/ml ; 0.226 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.14
Solubility : 0.948 mg/ml ; 0.00726 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 4765-77-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4765-77-9 ]

* 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 [ 4765-77-9 ]
  • Downstream synthetic route of [ 4765-77-9 ]

[ 4765-77-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1193-21-1 ]
  • [ 4765-77-9 ]
YieldReaction ConditionsOperation in experiment
57% With hydrogenchloride In 1,4-dioxane; ethanol; water Intermediate 1: 6-Chloro-3H-pyrimidin-4-one
A mixture of 4,6-dichloropyrimidine (Aldrich; 10.00 g, 67.1 mmol), concentrated hydrochloric acid (50 mL), water (50 mL) and dioxane (50 mL) was heated at about 70° C. for 6 h, and then allowed to cool to room temperature.
This gave a pink solution.
The solvents were evaporated under reduced pressure (vacuum pump) to give a pink solid.
Ethanol (50 mL) was added and the mixture was heated.
The solid went into solution.
The solution was placed in a warm bath (about 50° C.) and allowed to cool slowly.
After standing over the weekend, the off-white solid was filtered off to give 6-chloro-3H-pyrimidin-4-one (5.02 g, 57percent), mp 193-194° C. (lit. mp 192-193° C. in D. J. Brown and J. S. Harper J. Chem. Soc. 1961, 1298-1303).
1H NMR (d6-DMSO) δ 6.50 (s, 1H), 8.19 (s, 1H), 13.00 (br s, 1H).
56% With hydrogenchloride In 1,4-dioxane; water at 70℃; for 6 h; A solution of 4,6-dichloropyrimidine (2 g, 13.42 mmol) in a mixture of 4N HC1 (10.49 mL, 121 mmol)- 1,4-dioxane (10 mL)-water (10 mL) was heated to 70 CC for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to afford a pink solid. Ethanol (25 mL) was added to thesolid and the mixture was heated at 50 °C until the solid dissolved. The resulting pink solution was left overnight at room temperature and the precipitation formed was filtered and dried under vacuum to afford 6-chloropyrimidin-4(3B)-one (1 g, 7.51 mmol, 56percent yield) as an off-white solid. LCMS (ESI)m/e 130.8 [(M+H), calcd for C4H4C1N2O, 130.91; LC/MS retention time (Method C): tR = 0.51 mm.
Reference: [1] Journal of the Chinese Chemical Society, 2013, vol. 60, # 1, p. 27 - 34
[2] Patent: US2009/149466, 2009, A1,
[3] Patent: WO2017/59080, 2017, A1, . Location in patent: Page/Page column 288; 289
  • 2
  • [ 26452-81-3 ]
  • [ 4765-77-9 ]
Reference: [1] Helvetica Chimica Acta, 1959, vol. 42, p. 1317,1321
  • 3
  • [ 4765-77-9 ]
  • [ 88982-91-6 ]
Reference: [1] Patent: EP1333029, 2003, A1,
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