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[ CAS No. 831203-15-7 ] {[proInfo.proName]}

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Chemical Structure| 831203-15-7
Chemical Structure| 831203-15-7
Structure of 831203-15-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 831203-15-7 ]

CAS No. :831203-15-7 MDL No. :MFCD11111850
Formula : C6H4BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :XLGDBMBECTZVKI-UHFFFAOYSA-N
M.W : 198.02 Pubchem ID :45789784
Synonyms :

Calculated chemistry of [ 831203-15-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.25
TPSA : 49.57 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) : -7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 0.58
Log Po/w (WLOGP) : 1.31
Log Po/w (MLOGP) : 0.09
Log Po/w (SILICOS-IT) : 1.83
Consensus Log Po/w : 1.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.81
Solubility : 3.06 mg/ml ; 0.0154 mol/l
Class : Very soluble
Log S (Ali) : -1.19
Solubility : 12.7 mg/ml ; 0.064 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.198 mg/ml ; 0.001 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 831203-15-7 ]

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 [ 831203-15-7 ]

* 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 [ 831203-15-7 ]
  • Downstream synthetic route of [ 831203-15-7 ]

[ 831203-15-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1305329-97-8 ]
  • [ 831203-15-7 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With trifluoroacetic acid In dichloromethane at 20℃; for 4 h;
Stage #2: With sodium hydrogencarbonate In water
To the solution of (5-bromo-pyrimidin-2-yl)-cyano-acetic acid tert-butyl ester (3.2 g, 10 mmol) in dichloromethane (30 mL) was added trifluoroacetic acid (10 mL). The reaction mixture was stirred at room temperature for 4 h. The mixture was concentrated. To the residue was added water, and the "pH" of the mixture was adjusted to neutral by saturated aqueous NaHCO3 solution. The mixture was then extracted with ethyl acetate. Organic layer was separated, the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:3, 1:2, 1;1) to give (5-bromo-pyrimidin-2-yl)-acetonitrile as a white solid (1.2 g, 71percent).
67.4% at 70℃; for 2 h; A mixture of tert-butyl 2- (5-bromopyrimidin-2-yl) -2-cyanoacetic acid tert-butyl ester (3.068,10.301111111), 4111001 /Of hydrochloric acid (20 mL) and acetic acid (20 mL)Followed by adding to 100 mL of the reaction flask,The reaction was warmed to 70 ° (2 hours to stop the reaction, the reaction solution was poured directly into ice water (150 mL)Ethyl acetate (50 mL X 3). The organic phases were combined, washed successively with water (50 mL X 3) and saturated brine (50 mL), dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting crude product was directly subjected to silica gel column The title compound (yellow solid, 1.37 g, 67.40percent) was obtained by chromatography and purification (petroleum ether / ethyl acetate (ν / ν) = 5/1)
Reference: [1] Patent: US2011/118283, 2011, A1, . Location in patent: Page/Page column 14
[2] Patent: CN106674207, 2017, A, . Location in patent: Paragraph 0201-0204
  • 2
  • [ 65364-66-1 ]
  • [ 831203-15-7 ]
YieldReaction ConditionsOperation in experiment
43%
Stage #1: With sodium chloride In water; dimethyl sulfoxide at 120℃; for 3 h;
Stage #2: With sodium hydroxide In water
Synthesis of(5-bromopyrιmιdιn-2-yl)acetomtrιleTo 2 7Og of ethyl (5-bromopyπmidin-2-yl)(cyano)acetate (9 970 mmol) in dimethylsulfoxyde (20 ml) was added 0 584g of sodium chloride (9 970 mmol) and 0 18mL of water (9 970 mmol) The mixture was heated at 1200C under a nitrogen atmosphere for 3 hours The mixture was poured into water ( 30OmL) and the resultant precipitate was collected by filtration to give 5-bromopynmidin-2- yl)acetomtπle (0 6g , yield = 30percent)The clear yellow filtrate was salted by the addition of a saturated solution of sodium chloride, neutralided with sodium hydroxide, to give a red solution which was then extracted with dichloromethane The organic phase was collected, dried over magnesium sulphate, and evaporated in vacuo to give a dark oil, wich was purified by flash chromatography using 2/1 heptane/ ethyl acetate as eluent, yieldidng to 5 bromopyπmidm-2-yl)acetonitπle (0 9g , yield = 43percent) 1H NMR S (PPm7 CDCl3) 9 0 (s, 2H), 425 (s, 2H)
43%
Stage #1: With sodium chloride In water; dimethyl sulfoxide at 120℃; for 3 h;
Stage #2: With sodium hydroxide In water
Synthesis of(5-bromopyrimidin-2-yl)acetonitrileTo 2.7Og of ethyl (5-bromopyrimidin-2-yl)(cyano)acetate (9.970 mmol) in dimethylsulfoxyde (20 ml) was added 0.584g of sodium chloride (9.970 mmol) and 0.18mL of water (9.970 mmol). The mixture was heated at 1200C under a nitrogen atmosphere for 3 hours. The mixture was poured into water ( 30OmL) and the resultant precipitate was collected by filtration to give 5-bromopyrimidin-2- yl)acetonitrile (0.6g , yield = 30percent).The clear yellow filtrate was salted by the addition of a saturated solution of sodium chloride, neutralided with sodium hydroxide, to give a red solution which was then extracted with dichloromethane. The organic phase was collected, dried over magnesium sulphate, and evaporated in vacuo to give a dark oil, wich was purified by flash chromatography using 2/1 heptane/ ethyl acetate as eluent, yieldidng to 5-bromopyrimidin-2-yl)acetonitrile (0.9g , yield = 43percent). 1H NMR δ (ppm, CDCl3) : 9.0 (s, 2H); 4.25 (s, 2H).
Reference: [1] Patent: WO2006/117356, 2006, A1, . Location in patent: Page/Page column 29
[2] Patent: WO2006/117358, 2006, A1, . Location in patent: Page/Page column 37
  • 3
  • [ 1116-98-9 ]
  • [ 32779-36-5 ]
  • [ 831203-15-7 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: With sodium hydride In dimethyl sulfoxide at 20℃; for 1 h; Inert atmosphere
Stage #2: at 20℃; for 8 h; Inert atmosphere
Stage #3: With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 16 h;
To a suspension of sodium hydride (53 mg (60percent oil suspension), 1.34 mmol) in DMSO (2 ml) at room temperature under a nitrogen atmosphere was added tert-butyl cyanoacetate (197 mg, 39 mmol) in DMSO (1 ml) was added dropwise over 15 minutes and then stirred at room temperature for 1 hour.5-Bromo-2-chloropyrimidine (100 mg, 0.52 mmol) was added to the reaction solution, and the mixture was stirred at room temperature for 8 hours. Next, a saturated aqueous solution of ammonium chloride was added to the reaction system, extracted with ethyl acetate, washed with water, and then concentrated under reduced pressure to obtain a crude product.Subsequently, trifluoroacetic acid (1.8 ml) was added to a solution of the dried crude product in dichloromethane (2.3 ml) at 0 ° C., and the mixture was stirred for 1 hour and then allowed to warm to room temperature and stirred for 15 hours did.The reaction solution was neutralized with a saturated aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was filtered and concentrated under reduced pressure to obtain a crude product of (5-bromopyrimidin-2-yl) acetonitrile.The obtained crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain (5-bromopyrimidin-2-yl) acetonitrile. Yield 46 mg, yield 45percent, white solid.
Reference: [1] Patent: JP2017/178911, 2017, A, . Location in patent: Paragraph 0152; 0153
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