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[ CAS No. 870521-33-8 ] {[proInfo.proName]}

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Chemical Structure| 870521-33-8
Chemical Structure| 870521-33-8
Structure of 870521-33-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 870521-33-8 ]

CAS No. :870521-33-8 MDL No. :MFCD07375148
Formula : C8H12BN3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :KFYQOIHLZBDFBU-UHFFFAOYSA-N
M.W : 209.01 Pubchem ID :46864007
Synonyms :

Calculated chemistry of [ 870521-33-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 57.58
TPSA : 78.71 Ų

Pharmacokinetics

GI absorption : Low
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) : -8.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.81
Log Po/w (WLOGP) : -2.39
Log Po/w (MLOGP) : -1.74
Log Po/w (SILICOS-IT) : -1.68
Consensus Log Po/w : -1.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.79
Solubility : 33.9 mg/ml ; 0.162 mol/l
Class : Very soluble
Log S (Ali) : -0.36
Solubility : 90.5 mg/ml ; 0.433 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.74
Solubility : 38.4 mg/ml ; 0.184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.27

Safety of [ 870521-33-8 ]

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 [ 870521-33-8 ]

* 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 [ 870521-33-8 ]
  • Downstream synthetic route of [ 870521-33-8 ]

[ 870521-33-8 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 110-91-8 ]
  • [ 1003845-06-4 ]
  • [ 870521-33-8 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine In ethanol at 20℃; for 1 h; 2-Chloropyrimidin-5-ylboronic acid (1 g, 6.32 mmol), morpholine (2.19 mL,25.26 mmol) and triethylamine (0.88 mL, 6.32 mmol) were stirred in ethanol (25 mL) at20°C for 1 h. Water (50 mL) was slowly added to the reaction mixture. The resultingprecipitate was filtered and washed with water to afford the title compound (950 mg,70percent) as a cream solid. H (250 MHz, DMSO-d6) 8.63 (s, 2H), 8.05 (s, 2H), 3.68 (ddd, J23.4, 5.7, 3.9 Hz, 8H).
70% With triethylamine In ethanol at 20℃; for 1 h; A solution of (2-chloropyrimidin-5-yl)boronic acid (1 g, 6.32 mmol), morpholine (2.19 mL, 25.26 mmol) and triethylamine (0.9 mL, 6.32 mmol) in ethanol (25 mL) was stirred at 20°C for 1 h. Water (50 mL) was slowly added to the reaction mixture to form a precipitate that was collected by filtration, to afford the title compound (950 mg, 70percent) ascream solid. H (250 MHz, DMSO-d6) 8.63 (s, 2H), 8.05 (s, 2H), 3.68 (ddd, J23.4, 5.7,3.9 Hz, 8H). LCMS m/z 210 [M+H].
70% With triethylamine In ethanol at 20℃; for 1 h; Inert atmosphere A solution of (2-chloropyrimidin-5-yl)boronic acid (1 g, 6.32 mmol), morpholine (2.19 mL, 25.26 mmol) and triethylamine (0.9 mL, 6.32 mmol) in ethanol (25 mL) was stirred at 20°C for 1 h. Water (50 mL) was slowly added to the reaction mixture to form a precipitate that was collected by filtration, to afford the title compound as a cream solid (950 mg, 70percent). δΗ (250 MHz, DMSO-d6) 8.63 (s, 2H), 8.05 (s, 2H), 3.68 (ddd, J23.4, 5.7, 3.9 Hz, 8H). LCMS(ES+) 210 (M+H)+.
70% With triethylamine In ethanol at 20℃; for 1 h; A solution of (2-chloropyrimidin-5-yl)boronic acid (1 g, 6.32 mmol), morpholine (2.19 mL, 25.26 mmol) and triethylamine (0.9 mL, 6.32 mmol) in ethanol (25 mL) was stirred at 20°C for 1 h. Water (50 mL) was slowly added to the reaction mixture to form a precipitate that was collected by filtration, to afford the title compound as a cream solid (950 mg, 70percent). δΗ (250 MHz, DMSO-d6) 8.63 (s, 2H), 8.05 (s, 2H), 3.68 (ddd, J23.4, 5.7, 3.9 Hz, 8H). LCMS(ES+) 210.0 (M+H)+.
70% With triethylamine In ethanol at 20℃; for 1 h; A solution of(2-chloropyrimidin-5-yl)boronic acid (1 g, 6.32 mmol), morpholine (2.19 mL, 25.26 mmol) and triethylamine (0.9 mL, 6.32 mmol) in ethanol (25 mL) was stirred at 20°C for 1 h. Water (50 mL) was slowly added to the reaction mixture to form a precipitate that was collected by filtration, to afford the title compound as a cream solid(950 mg, 70percent). oH (250 MHz, DMSO-d6) 8.63 (s, 2H), 8.05 (s, 2H), 3.68 (ddd, J23.4, 5.7, 3.9 Hz, 8H). LCMS(ES) 210 (M+H).
68% With triethylamine In ethanol at 80℃; for 5 h; A mixture of 2-chloropyrimidin-5-ylboronic acid (3 g, 19.0 mmol), morpholine (1.66 mL, 19 mmol) and triethylamine (1.67 mL, 19.19 mmol) in EtOH (20 mL) was stirred at 80°C for 5 h. LCMS indicated completion of the reaction. The reaction mixturewas concentrated in vacuo and the residue was taken up in ethanol (approximately 5 mL). Diethyl ether was added, and the triethylamine hydrochloride salt that crystallised out was filtered and discarded. The filtrate was concentrated in vacuo and water (approximately 10 mL) was added. The mixture was placed in a refrigerator for 1 h, after which time the resulting solid was filtered off, washed with the minimum amount of water and dried bysuction, to give the title compound (2.7 g, 68percent) as an off-white solid. oH (DMSO-d6)8.64 (s, 2H), 8.08 (s, 2H), 3.73 (m, 4H), 3.65 (m, 4H). LCMS (ES+) 210 (M+H), RT0.15 minutes.
68% With triethylamine In ethanol at 80℃; for 5 h; A mixture of 2-chloropyrimidin-5-ylboronic acid (3 g, 19.0 mmol), morpholine (1.66 mL, 19.0 mmol) and triethylamine (1.67 mL, 19.2 mmol) in EtOH (20 mL) wasstirred at 80°C for 5 h. The reaction mixture was concentrated in vacuo and the residue was taken up in Et20 (approximately 5 mL). Et20 was added, and the triethylamine hydrochloride salt that crystallised out was filtered and discarded. The filtrate was concentrated in vacuo and water (approximately 10 mL) was added. The mixture was placed in a refrigerator for 1 h, after which time the resulting solid was filtered off, washed with the minimum amount of water and dried by suction, to give the title compound (2.7 g, 68percent) as an off-white solid. oH (DMSO-d6) 8.64 (s, 2H), 8.08 (s, 2H), 3.73 (m, 4H), 3.65 (m, 4H). LCMS (ESj 210 (M+H), RT 0.15 minutes.
68% With triethylamine In ethanol at 80℃; for 5 h; INTERMEDIATE 4 2-(Morpholin-4-yl)pyrimidin-5 -ylboronic acidA mixture of 2-chloropyrimidin-5-ylboronic acid (3.0 g, 19.0 mmol), morpholine (1.66 mL, 19.0 mmol) and triethylamine (1.67 mL, 19.2 mmol) in EtOH (20 mL) was stirred at 80°C for 5 h. The reaction mixture was concentrated in vacuo and the residue was taken up in Et20 (approximately 5 mL). Et20 was added, and the triethylamine hydrochloride salt that crystallised out was filtered and discarded. The filtrate was concentrated in vacuo and water (approximately 10 mL) was added. The mixture was placed in a refrigerator for 1 h, after which time the resulting solid was filtered off,washed with the minimum amount of water and dried by suction, to give the title compound (2.7 g, 68percent) as an off-white solid. H (400 MHz, DMSO-d6) 8.64 (s, 2H), 8.08 (s, 2H), 3.73 (m, 4H), 3.65 (m, 4H). LCMS (ESj 210 (M+H), RT 0.15 minutes.
68% With triethylamine In ethanol at 80℃; for 5 h; INTERMEDIATE 5 2- (Morpholin-4- yl)p yrimidin- 5 - ylboronic acid A mixture of 2-chloropyrimidin-5-ylboronic acid (3 g, 19.0 mmol), morpholine (1.66 mL, 19.0 mmol) and triethylamine (1.67 mL, 19.2 mmol) in EtOH (20 mL) was stirred at 80°C for 5 h. The reaction mixture was concentrated in vacuo and the residue was taken up in Et20 (approximately 5 mL). Et20 was added, and the triethylamine hydrochloride salt that crystallised out was filtered and discarded. The filtrate was concentrated in vacuo and water (approximately 10 mL) was added. The mixture was placed in a refrigerator for 1 h, after which time the resulting solid was filtered off, washed with the minimum amount of water and dried by suction, to give the title compound (2.7 g, 68percent) as an off-white solid. δΗ (DMSO-d6) 8.64 (s, 2H), 8.08 (s, 2H), 3.73 (m, 4H), 3.65 (m, 4H). LCMS (ES+) 210 (M+H)+, RT 0.15 minutes.
68% With triethylamine In ethanol at 80℃; for 5 h; INTERMEDIATE 3
2-(Morpholin-4-yl)pyrimidin-5 -ylboronic acid
A mixture of 2-chloropyrimidin-5 -ylboronic acid (3.0 g, 19.0 mmol), morpholine (1.66 mL, 19.0 mmol) and triethylamine (1.67 mL, 19.2 mmol) in EtOH (20 mL) was stirred at 80°C for 5 h. The reaction mixture was concentrated in vacuo and the residue was taken up in Et20 (approximately 5 mL). Et20 was added, and the triethylamine hydrochloride salt that crystallised out was filtered and discarded. The filtrate was concentrated in vacuo and water (approximately 10 mL) was added. The mixture was placed in a refrigerator for 1 h, after which time the resulting solid was filtered off, washed with the minimum amount of water and dried by suction, to give the title compound (2.7 g, 68percent) as an off-white solid. δΗ (400 MHz, DMSO-dg) 8.64 (s, 2H), 8.08 (s, 2H), 3.73 (m, 4H), 3.65 (m, 4H). LCMS (ES+) 210 (M+H)+, RT 0.15 minutes.

Reference: [1] Patent: WO2015/86506, 2015, A1, . Location in patent: Page/Page column 131
[2] Patent: WO2015/86512, 2015, A1, . Location in patent: Page/Page column 102
[3] Patent: WO2015/86527, 2015, A1, . Location in patent: Page/Page column 114; 115
[4] Patent: WO2015/86526, 2015, A1, . Location in patent: Page/Page column 147
[5] Patent: WO2015/86525, 2015, A1, . Location in patent: Page/Page column 121; 122
[6] Patent: WO2014/9295, 2014, A1, . Location in patent: Page/Page column 128; 129
[7] Patent: WO2015/86502, 2015, A1, . Location in patent: Page/Page column 82; 83
[8] Patent: WO2015/86511, 2015, A1, . Location in patent: Page/Page column 74; 75
[9] Patent: WO2015/86501, 2015, A1, . Location in patent: Page/Page column 89
[10] Patent: WO2015/86496, 2015, A1, . Location in patent: Page/Page column 74
  • 2
  • [ 84539-22-0 ]
  • [ 870521-33-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 77 - 105
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