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[ CAS No. 936250-22-5 ] {[proInfo.proName]}

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Chemical Structure| 936250-22-5
Chemical Structure| 936250-22-5
Structure of 936250-22-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 936250-22-5 ]

CAS No. :936250-22-5 MDL No. :MFCD07375147
Formula : C4H6BN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CGHYQZASLKERLV-UHFFFAOYSA-N
M.W : 138.92 Pubchem ID :17750211
Synonyms :

Calculated chemistry of [ 936250-22-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 36.26
TPSA : 92.26 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) : -8.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -1.24
Log Po/w (WLOGP) : -2.25
Log Po/w (MLOGP) : -2.4
Log Po/w (SILICOS-IT) : -2.19
Consensus Log Po/w : -1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.3
Solubility : 69.9 mg/ml ; 0.503 mol/l
Class : Very soluble
Log S (Ali) : -0.2
Solubility : 87.3 mg/ml ; 0.628 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.16
Solubility : 97.0 mg/ml ; 0.698 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 936250-22-5 ]

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 [ 936250-22-5 ]

* 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 [ 936250-22-5 ]
  • Downstream synthetic route of [ 936250-22-5 ]

[ 936250-22-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 883231-25-2 ]
  • [ 936250-22-5 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogenchloride In water Example 17
2-Aminopyrimidin-5-ylboronic acid III
To a mixture of [2-[(tert-butoxycarbonyl)amino]pyrimidin-5-yl]boronic acid 12 (40.0 kg, 49 wt percent by HPLC, 82.0 mol) in water (245 kg) was added concentrated hydrochloric acid (39.6 L) while maintaining the temperature below 30° C.
The reaction mixture was stirred for 12 h and was then cooled to 10° C.
The pH of the mixture was adjusted to 6.5 by addition of 50percent aqueous sodium hydroxide solution while maintaining the temperature below 15° C. and the mixture was then stirred for 1 h.
Water (69.0 kg) was added and the mixture was aged for 30 min.
The resulting slurry was filtered and the cake was dried under vacuum at 50° C. to afford 2-aminopyrimidin-5-ylboronic acid III (10.2 kg, 90percent yield).
1H NMR (300 MHz, DMSO-d6) δ 8.50 (s, 2H), 7.97 (s, 2H), 6.74 (s, 2H).
Reference: [1] Patent: US2014/100366, 2014, A1, . Location in patent: Page/Page column
  • 2
  • [ 7752-82-1 ]
  • [ 5419-55-6 ]
  • [ 936250-22-5 ]
YieldReaction ConditionsOperation in experiment
42% With hydrogenchloride; n-butyllithium; lithium hexamethyldisilazane In tetrahydrofuran; methanol; tert-butyl methyl ether; water By the alternative synthetic route in Scheme 8, to a 3-L flask under nitrogen was charged tetrahydrofuran (1055 mL), followed by 5-bromopyrimidine-2-amine 9 (70.0 g, 0.40 mol).
The mixture was cooled to a temperature between -60° C. and -70° C. and lithium bis(trimethylsilyl)amide (LiHMDS) (1M in tetrahydrofuran, 483 mL, 0.483 mol) was charged over 30 min while maintaining the temperature between -60° C. and -70° C.
The mixture was stirred at -60° C. to -70° C. for 1 h. n-Butyllithium (2.5 M in hexanes, 515 mL, 1.29 mol) was charged over 1 h while maintaining the temperature between -60° C. and -70° C., and the reaction mixture was then aged for 2 h.
Additional n-butyllithium (2.5 M in hexanes, 48 mL, 0.12 mol) was charged over 15 min while maintaining the temperature between -60° C. and -70° C., and the reaction mixture was stirred for 1 h.
To the mixture was added triisopropyl borate (91.0 g, 0.48 mol) over 1 h while maintaining the temperature between -60° C. and -70° C., and the reaction mixture was stirred for 1 h.
The mixture was then allowed to warm to 0-5° C. and water (700 mL) was added over 1 h.
After being aged at 0-5° C. for 30 min, the resulting layers were separated.
To the aqueous layer was added water (420 mL) over 30 min, followed by addition of tert-butyl methyl ether (822 mL).
The mixture was allowed to warm to 20-25° C. and was stirred for 30 min.
The layers were separated and the aqueous layer was washed with tert-butyl methyl ether (5*700 mL).
The aqueous layer was cooled to 0-5° C., and 35percent aqueous hydrochloric acid solution (137 mL) was added over 1 h while maintaining the temperature between 0-5° C.
The mixture was stirred at 0-5° C. for 1.5 h, filtered, washed with water (14 mL) and the cake was dried under vacuum at 45-50° C. to afford the crude product (26.7 g).
The crude product was charged to a 5-L flask, followed by addition of methanol (908 mL), and the mixture was stirred at room temperature (rt) for 20 min.
The mixture was warmed to 65° C. and stirred for 1.5 h.
To the mixture was added water (2136 mL) over 2 h and the suspension was stirred for 1.5 h.
The mixture was cooled to 20° C. and stirred for 14 h.
The solid was collected by filtration and the filter cake was washed with water (13 mL), dried under vacuum at 45-50° C. for 12 h to afford 2-aminopyrimidin-5-ylboronic acid III (23.6 g, 42percent yield)
Reference: [1] Patent: US2014/100366, 2014, A1, . Location in patent: Page/Page column
  • 3
  • [ 5419-55-6 ]
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Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 1, p. 95 - 99
  • 4
  • [ 402960-38-7 ]
  • [ 936250-22-5 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 10, p. 774 - 779
  • 5
  • [ 936250-22-5 ]
  • [ 1032757-58-6 ]
  • [ 1032754-93-0 ]
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 3, p. 416 - 426
  • 6
  • [ 71-23-8 ]
  • [ 936250-22-5 ]
  • [ 1032757-58-6 ]
  • [ 1032754-93-0 ]
Reference: [1] Patent: US2014/100366, 2014, A1, . Location in patent: Page/Page column
  • 7
  • [ 71-23-8 ]
  • [ 936250-22-5 ]
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  • [ 1032754-93-0 ]
Reference: [1] Patent: US2014/100366, 2014, A1, . Location in patent: Page/Page column
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