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[ CAS No. 89581-38-4 ] {[proInfo.proName]}

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Chemical Structure| 89581-38-4
Chemical Structure| 89581-38-4
Structure of 89581-38-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 89581-38-4 ]

CAS No. :89581-38-4 MDL No. :MFCD11111606
Formula : C6H5BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :XILAKTMDKMVJQV-UHFFFAOYSA-N
M.W : 217.02 Pubchem ID :45790831
Synonyms :

Calculated chemistry of [ 89581-38-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.01
TPSA : 52.08 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) : -7.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : -0.02
Log Po/w (WLOGP) : 1.03
Log Po/w (MLOGP) : 0.32
Log Po/w (SILICOS-IT) : 1.41
Consensus Log Po/w : 0.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.44
Solubility : 7.8 mg/ml ; 0.0359 mol/l
Class : Very soluble
Log S (Ali) : -0.62
Solubility : 51.6 mg/ml ; 0.238 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.56 mg/ml ; 0.00258 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 89581-38-4 ]

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 [ 89581-38-4 ]

* 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 [ 89581-38-4 ]
  • Downstream synthetic route of [ 89581-38-4 ]

[ 89581-38-4 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 89581-38-4 ]
  • [ 14080-23-0 ]
Reference: [1] Annales de Chimie (Cachan, France), 1960, vol. <13>5, p. 351,399,402
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 250
  • 2
  • [ 89581-38-4 ]
  • [ 38275-60-4 ]
Reference: [1] Annales de Chimie (Cachan, France), 1960, vol. <13>5, p. 351,399,402
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 250
  • 3
  • [ 67-56-1 ]
  • [ 37131-87-6 ]
  • [ 89581-38-4 ]
YieldReaction ConditionsOperation in experiment
67% for 0.25 h; Reflux To a solution of 5-bromopyrimidine-2-carboxylic acid (3.22 g, 15.9 mmol) in MeOH (50 mL) at room temperature was added acetyl chloride (4.0 mL, 56.3 mmol). The reaction mixture was heated to reflux for 15 min, cooled to room temperature and concentrated under reduced pressure. The reaction mixture was diluted with saturated NaHCC>3 (30 mL) and EtOAc, and transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4 x) and the combined organic extracts were washed with brine (1 x), dried over MgS04, filtered, and concentrated to give methyl 5- bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol, 67 percent yield) as a white solid. LC/MS (ESI) m/z = 216.9 (M+H). Calculated for 0ΒΓΝ202 216.0
67% for 0.25 h; Reflux To a solution of 5-bromopyrimidine-2-carboxylic acid (3.22 g, 15.9 mmol) in MeOH (50 mL) at room temperature was added acetyl chloride (4.0 mL, 56.3 mmol). The reaction mixture was heated to reflux for 15 min, cooled to room temperature and concentrated under reduced pressure. The reaction mixture was diluted with saturated NaHCO3 (30 mL) and EtOAc, and transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4 x) and the combined organic extracts were washed with brine (1 x), dried over MgSO4, filtered, and concentrated to give methyl 5- bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol, 67percent yield) as a white solid. LC/MS (ESI+) m/z = 216.9 (M+H). Calculated for C6H5BrN2O2216.0
57% at 0 - 20℃; for 18 h; Preparation 65 5-Bromo-pyrimidine-2-carboxylic acid methyl ester Fuming hydrochloric acid was passed through an ice-cooled SOTUTIBN OF THE- product of preparation 64 (5. 5g. 27mmol) in methanol (50mL) until saturated The reaction mixture was warmed to room temperature and was stirred for 18- hours. The solvent was then evaporated under reduced pressure and. the- residue was dissolved in dichloromethane, washed with water and sodium HYDROGEN CARBONATE SOLUTION, DRIED-OVER MAGNESIUM SULFATE. AND CONCENTRATED IN-: O AFFORD THE"TITLE compound as yellow. solid in 57percent yield, 3.5g. HNMR (CDC) 3. 400MHZ) .sect. : 4, 65 (s, 3H), 9. 00 (s, 2H). MS AP +
Reference: [1] Patent: WO2014/138484, 2014, A1, . Location in patent: Page/Page column 185; 186
[2] Patent: WO2016/22724, 2016, A1, . Location in patent: Page/Page column 328
[3] Patent: WO2005/28452, 2005, A1, . Location in patent: Page/Page column 88
[4] Patent: US2010/216806, 2010, A1, . Location in patent: Page/Page column 96
  • 4
  • [ 67-56-1 ]
  • [ 38275-57-9 ]
  • [ 89581-38-4 ]
YieldReaction ConditionsOperation in experiment
71% With hydrogenchloride In water at 80℃; for 2 h; Inert atmosphere To a solution of 5-bromopyrimidine-2-carbonitrile (3.0 g, 16 mmol) in MeOH (20 mL) was added concentrated HCl (19 mL).
The reaction mixture was heated at 80° C. for 2 h.
Upon cooling to rt, a precipitate formed.
Filtration provided the desired product as a white solid (2.5 g, 71percent). MS (ESI): mass calcd. for C6H5BrN2O2, 216.0; m/z found, 217.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 9.20 (s, 2H), 3.92 (s, 3H).
Reference: [1] Patent: US2014/275096, 2014, A1, . Location in patent: Paragraph 0126; 0169; 0170
  • 5
  • [ 67-56-1 ]
  • [ 1013335-78-8 ]
  • [ 89581-38-4 ]
YieldReaction ConditionsOperation in experiment
294 mg at 0℃; for 2 h; To a solution of 5-bromopyrimidine-2-carboxylic acid (500 mg, 2.47 mmol) in DCM (5.0 mL), in a two-necked flask equipped with a bubbler, was added oxalyl chloride (0.23 mL, 2.72 mmol) and two drops of DMF at room temperature. After stirring for 1.5 h, the solvent was removed in vacuo. The acyl chloride was dissolved in CH2C12 (5.0 mL) and added MeOH (0.20 mL, 4.93 mmol) at 0 °C. After stirring for 2 h, the reaction mixture was quenched by adding saturated NaHCC solution. The crude products were extracted with CH2C12 (x3), and the combined organic extracts were washed with brine, dried (MgS04), and concentrated in vacuo. The residue was purified by flash column chromatography (hexane/EtOAc = 3/1 to 2/1) to afford desired methyl 5-bromopyrimidine-2-carboxylate (294 mg, 90percent) as a white solid. NMR (300 MHz, CDCh) δ 9.01 (s, 2H), 4.10 (s, 3H).
Reference: [1] Patent: WO2018/136935, 2018, A1, . Location in patent: Paragraph 00770; 00772
  • 6
  • [ 37131-87-6 ]
  • [ 89581-38-4 ]
Reference: [1] Patent: WO2018/136935, 2018, A1,
  • 7
  • [ 89581-38-4 ]
  • [ 73418-88-9 ]
Reference: [1] Patent: US2012/165343, 2012, A1,
  • 8
  • [ 89581-38-4 ]
  • [ 22433-12-1 ]
YieldReaction ConditionsOperation in experiment
19% With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 20℃; An solution of NaBH4 (510 mg, 2.70 mmol) in H2O (10 mL) was introduced drop-wise to a solution of methyl 5-bromopyrimidine-2-carboxylate (3.05 g, 14.1 mmol) in THF (100 mL) at 0° C.
The mixture was allowed to warm slowly to RT overnight.
The majority of the THF was evaporated, and the resulting residue was diluted with EtOAc (200 mL).
The organic fraction was washed with brine (200 mL), dried (MgSO4) and purified over silica, eluting with 0-60percent EtOAc:n-heptane) to afford i (510 mg, 19percent). MS: 189.0 & 191.0; 1:1 [M+H]+.
Reference: [1] Patent: US2013/252938, 2013, A1, . Location in patent: Paragraph 0596
  • 9
  • [ 89581-38-4 ]
  • [ 87362-30-9 ]
YieldReaction ConditionsOperation in experiment
72% With hydrazine hydrate In ethanol at 20℃; for 1 h; Inert atmosphere To a slurry of methyl 5-bromopyrimidine-2-carboxylate (1.0 g, 4.6 mmol) in EtOH (3.6 mL) was added hydrazine monohydrate (0.46 mL, 9.2 mmol).
The reaction mixture was stirred at rt for 1 h.
The mixture was filtered, and the collected solid was washed with additional EtOH to provide the desired product as a beige solid (720 mg, 72percent). MS (ESI): mass calcd. for C5H5N4O, 216.0; m/z found, 217.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 10.15 (s, 1H), 9.18-9.08 (s, 2H), 4.67 (s, 2H).
Reference: [1] Patent: US2014/275096, 2014, A1, . Location in patent: Paragraph 0126; 0171
  • 10
  • [ 89581-38-4 ]
  • [ 74-89-5 ]
  • [ 1346819-04-2 ]
Reference: [1] Patent: WO2011/138751, 2011, A2, . Location in patent: Page/Page column 101
[2] Patent: US2012/46285, 2012, A1, . Location in patent: Page/Page column 35
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