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[ CAS No. 109299-78-7 ] {[proInfo.proName]}

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Chemical Structure| 109299-78-7
Chemical Structure| 109299-78-7
Structure of 109299-78-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 109299-78-7 ]

CAS No. :109299-78-7 MDL No. :MFCD03002366
Formula : C4H5BN2O2 Boiling Point : -
Linear Structure Formula :B(OH)2C(CH)3N2 InChI Key :HZFPPBMKGYINDF-UHFFFAOYSA-N
M.W : 123.91 Pubchem ID :2795193
Synonyms :
Chemical Name :Pyrimidin-5-ylboronic acid

Calculated chemistry of [ 109299-78-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 31.86
TPSA : 66.24 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) : -7.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.89
Log Po/w (WLOGP) : -1.84
Log Po/w (MLOGP) : -2.25
Log Po/w (SILICOS-IT) : -1.51
Consensus Log Po/w : -1.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.47
Solubility : 41.5 mg/ml ; 0.335 mol/l
Class : Very soluble
Log S (Ali) : -0.02
Solubility : 119.0 mg/ml ; 0.958 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.5
Solubility : 39.3 mg/ml ; 0.317 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 109299-78-7 ]

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 [ 109299-78-7 ]

* 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 [ 109299-78-7 ]
  • Downstream synthetic route of [ 109299-78-7 ]

[ 109299-78-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 109299-78-7 ]
  • [ 26456-59-7 ]
Reference: [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 2009, vol. 131, p. 4174 - 4175
  • 2
  • [ 1003015-89-1 ]
  • [ 14221-01-3 ]
  • [ 109299-78-7 ]
  • [ 26456-59-7 ]
  • [ 1134120-38-9 ]
  • [ 98511-61-6 ]
Reference: [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 2009, vol. 131, p. 4174 - 4175
  • 3
  • [ 75-05-8 ]
  • [ 109299-78-7 ]
  • [ 40805-79-6 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13246 - 13252
  • 4
  • [ 4595-59-9 ]
  • [ 109299-78-7 ]
YieldReaction ConditionsOperation in experiment
44%
Stage #1: With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane; toluene at -70 - -20℃; for 0.5 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane; toluene at -20 - 20℃;
Stage #3: With potassium hydroxide In water
5-Pyrimidineboronic acid; "BuLi (3.02 ml, 2M solution in hexane, 7.55 mmol) was added dropwise to a stirring solution of 5-bromopyrimidine (1 g, 6.29 mmol) and triisopropylborate (1.46 ml, 7.55 mmol) in anhydrous toluene (16 ml) and anhydrous THF (4 ml) at-70°C under a nitrogen atmosphere. The reaction mixture was stirred at-70°C for 30 mins and then removed from the cold bath. When the internal temp. reached-20°C, the reaction was quenched by the dropwise addition of 2M HCI (10 ml). The mixture was allowed to warm to RT and then separated. The aqueous phase was taken to pH 5.5 with 2M KOH and extracted into THF (3 x 25 ml). The combined organic extracts were dried (MgS04), filtered and concentrated in vacuo to provide a colourless solid. The solid was slurried in acetonitrile (2 ml), collected by filtration and dried on the sinter to give the target boronic acid as a brilliant white solid (340 mg, 44percent). 8H(MeOD; 250MHz) 8.98 (2H, s), 9.14 (1H, s).
Reference: [1] Synthetic Communications, 2003, vol. 33, # 5, p. 795 - 800
[2] Organic and Biomolecular Chemistry, 2004, vol. 2, # 6, p. 852 - 857
[3] Patent: WO2005/103019, 2005, A1, . Location in patent: Page/Page column 16
[4] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
[5] Patent: US2006/111394, 2006, A1, . Location in patent: Page/Page column 17
  • 5
  • [ 4595-59-9 ]
  • [ 121-43-7 ]
  • [ 109299-78-7 ]
YieldReaction ConditionsOperation in experiment
64% With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -15℃; To a solution of compound 5-bromopyrimidine (8 g, 50 mmol), trimethyl borate (4.6g, 60 mmol) in toluene and THF (150 mL,V/V=4: 1) was added n-BuLi (24 mL, 60 mmol, 2.5 M in hexane) at <n="135"/>-780C. The reaction mixture was stirred for 1 h at -780C, then warmed to -150C and quenched with 2 N HCl (50 mL, 100 mmol). The mixture was concentrated and purification by chromatography (MeOHrDCM=I : 10) to give pyrimidin-5-ylboronic acid (4 g, 64percent) as light yellow solid. MS (m/z) (IvT+H): 125.
Reference: [1] Patent: WO2009/155527, 2009, A2, . Location in patent: Page/Page column 133-134
  • 6
  • [ 109299-78-7 ]
  • [ 1227164-02-4 ]
  • [ 1227163-84-9 ]
Reference: [1] Patent: US2011/281894, 2011, A1, . Location in patent: Page/Page column 11
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