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[ CAS No. 947533-45-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 947533-45-1
Chemical Structure| 947533-45-1
Chemical Structure| 947533-45-1
Structure of 947533-45-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 947533-45-1 ]

CAS No. :947533-45-1 MDL No. :MFCD09835164
Formula : C4H2BrFN2 Boiling Point : -
Linear Structure Formula :- InChI Key :ANSMRNCOBLTNBO-UHFFFAOYSA-N
M.W : 176.97 Pubchem ID :26344048
Synonyms :

Calculated chemistry of [ 947533-45-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.69
TPSA : 25.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 1.8
Log Po/w (MLOGP) : 0.81
Log Po/w (SILICOS-IT) : 2.16
Consensus Log Po/w : 1.56

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.33
Solubility : 0.828 mg/ml ; 0.00468 mol/l
Class : Soluble
Log S (Ali) : -1.47
Solubility : 5.96 mg/ml ; 0.0337 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.78
Solubility : 0.293 mg/ml ; 0.00166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 947533-45-1 ]

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

Application In Synthesis of [ 947533-45-1 ]

* 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 [ 947533-45-1 ]
  • Downstream synthetic route of [ 947533-45-1 ]

[ 947533-45-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 947533-45-1 ]
  • [ 75-86-5 ]
  • [ 38275-55-7 ]
Reference: [1] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1123 - 1130
  • 2
  • [ 62802-42-0 ]
  • [ 947533-45-1 ]
YieldReaction ConditionsOperation in experiment
51% With trimethylsilyl bromide In propiononitrile at 150℃; for 1 h; Step A: To 2-chloro-5-fluoropyrimidine (2 mL, 22.18 mmol) were added propionitrile (20 mL) and bromotrimethylsilane (6 mL), and the mixture was heated in a sealed vial at 150° C. for 1 h. The mixture was allowed to cool, and then was concentrated under reduced pressure. The residue was partitioned between EtOAc and saturated aq NaHCO3 and the organic phase was dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in hexanes and cooled to -30° C. overnight to give a solid, which was collected by filtration to afford 2-bromo-5-fluoropyrimidine (2.03 g, 51percent). 1H NMR (300 MHz, CDCl3) δ 8.49 (s, 2H).
Reference: [1] Patent: US2012/53174, 2012, A1, . Location in patent: Page/Page column 44
  • 3
  • [ 2857-97-8 ]
  • [ 62802-42-0 ]
  • [ 947533-45-1 ]
YieldReaction ConditionsOperation in experiment
1.54 g at 150℃; for 1.5 h; 2-Chloro-5-fiuoro-pyrimidine (1.0 mL) was dissolved in DME (10 mL). TMS-Br (1.5 mL) was added and the mixture stirred at 150 °C in a closed vial for 1.5 h. The mixture was allowed to cool, then concentrated in vacuo. The residue was dissolved in CH2CI2 and filtered through a plug of silica. The filtrate was concentrated in vacuo to give a pale yellow liquid (1.54 g). This compound, 2-bromo-5-fiuoropyrimidine (containing some 2-chloro-5-fiuoro-pyrimidine), (0.75 g) was dissolved in triethylamine (7 mL) under an argon atmosphere. TMS-acetylene (0.6 mL) was added followed by bis(triphenylphosphine)palladium(II) dichloride (15 mg) and copper(I) iodide (30 mg). After heating the mixture at 50 °C 5 h, it was concentrated in vacuo. The residue was purified by flash chromatography (SiC^/Petroleum ether:EtOAc 95:5→5:95) and 5- fluoro-2-[2-(trimethylsilyl)ethynyl]pyrimidine was isolated as a colorless oil (300 mg, 38percent purity).
Reference: [1] Patent: WO2016/113335, 2016, A1, . Location in patent: Page/Page column 51; 52
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