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Quality Control of [ 1034924-06-5 ] Purity: 96% SDS Specification

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Product Details of [ 1034924-06-5 ]

CAS No. :	1034924-06-5
Formula :	C₅H₇BN₂O₂
M.W :	137.93
SMILES Code :	CC1=NC=C(C=N1)B(O)O
MDL No. :	MFCD07375144
InChI Key :	BTJLWJOEZRVRNL-UHFFFAOYSA-N
Pubchem ID :	45787274

Safety of [ 1034924-06-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 1034924-06-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.2
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	2.0
Molar Refractivity	36.82
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.24 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.49
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-1.54
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-1.84
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-1.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.76
Solubility	23.7 mg/ml ; 0.172 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.43
Solubility	50.8 mg/ml ; 0.368 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.9
Solubility	17.3 mg/ml ; 0.126 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.49 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.87

Application In Synthesis of [ 1034924-06-5 ]

* 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.

Downstream synthetic route of [ 1034924-06-5 ]

[ 1034924-06-5 ] Synthesis Path-Downstream 1~31

1
[ 1072854-55-7 ]
[ 1034924-06-5 ]
[ 1072855-06-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5618 - 5624.

2
[ 1034924-06-5 ]
[ 1420618-39-8 ]
[ 1420619-03-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 2-dicyclohexylphosphino-2?,6?-di-i-propoxy-1,1?-biphenyl; palladium diacetate; sodium carbonate; In 1,4-dioxane; at 125℃; for 3h;Microwave irradiation; Sealed tube; Inert atmosphere;	Compound 1-41 was prepared from compound 1-2 according to the following coupling procedures:[00773] Compound 1-2 (230 umol), boronic acid (690 umol, 3 eq.), sodium carbonate (1.15 mmol, 5 eq.),RuPhos (70 muetaiotaomicron?, 0.30 eq.), and palladium diacetate (35 umol, 0.15 eq.) were combined in a 2 mL microwave- reaction tube with a stir bar which was sealed with a septum. The atmosphere was purged three times with vacuum, backfilling with dry argon, then 1,4-dioxane (1.6 mL) and water (0.4 mL) were added. The reaction was subjected to microwave heating at 125 °C for 3h. The reaction mixture was diluted with DCM (ca. 30 mL), treated with silica gel (ca. 1 g) and concentrated; flash chromatography of this residue (on 15 g silica gel, eluting with a MeOH/DCM or EtOAc/hexanes gradient as required, approx. 750 mL total eluent) gave the product 1-41 as a light-yellow to off- white powder. ESI-MS m/z: 485.8 [M+H]+.

References: [1]Patent: WO2013/12915,2013,A1 .Location in patent: Paragraph 00772-00773.

3
[ 1198319-60-6 ]
[ 1034924-06-5 ]
[ 1470082-12-2 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 8834 - 8848.

4
[ 1034924-06-5 ]
[ 1494218-39-1 ]
[ 1494218-40-4 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9586 - 9600.

5
[ 1034924-06-5 ]
[ 1403396-19-9 ]
[ 1403396-97-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride-chloroform adduct; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 3h;	The compound (2.34 g, 6.59 mmol) obtained in Example 16-2), <strong>[1034924-06-5](2-methylpyrimidin-5-yl)boronic acid</strong> (1.00 g, 7.25 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex (0.54 g, 0.66 mmol), and potassium carbonate (2.73 g, 19.76 mmol) were dissolved in a mixed solvent of 1,4-dioxane (20 mL) and water (10 mL), and the mixture was stirred at 90°C for 3 h. The reaction mixture was cooled to room temperature and then diluted with ethyl acetate (150 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane = 50:50 to 100:0). The obtained partially purified product was dissolved in methanol (5 mL). 4 N hydrochloric acid-dioxane (2.39 mL) was added to the solution, and the mixture was stirred at room temperature for 2 h. The solvent was distilled off, and the residue was separated into organic and aqueous layers with methylene chloride (150 mL) and saturated aqueous sodium hydrogencarbonate (50 mL). The organic layer was washed with saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (591 mg, yield: 82percent) as a white solid. 1H-NMR (CDCl3) delta: 1.13 (2H, dd, J = 7.4, 3.5 Hz), 1.67 (2H, dd, J = 7.8, 3.5 Hz), 2.80 (3H, s), 7.48-7.61 (4H, m), 8.84 (2H, s)

References: [1]Patent: EP2700643,2014,A1 .Location in patent: Paragraph 0417.

6
[ 1034924-06-5 ]
[ 1610703-69-9 ]
[ 1610703-67-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere;	Into a 5-L 4-neck round-bottom flask purged and maintained with an inert atmosphere ofnitrogen was placed a solution of 6-chloro-9-ethyl-8-iodo-9H-purine (242 g, 784 mmol), <strong>[1034924-06-5](2-methylpyrimidin-5-yl)boronic acid</strong> (108 g, 783 mmol), potassium carbonate (162 g, 1.17 mol) and Pd(dppf)C12-DCM (32 g, 39 mmol) in dioxane (2.4 L) and water (480 mL). The resulting solution was stirred overnight at 90°C. The reaction mixture was cooled to room temperature, then extracted with 2 x 1.5 L of ethyl acetate. The organic extracts were combined, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/dichloromethane/ethyl acetate (5:1:1) providing 6-chloro-9-ethyl-8-(2-methylpyrimidin-5-yl)-9H-purine (Intermediate IV). ?H NMR (300 MHz, CDC13) 9.12 (s, 2 H), 8.80 (s, 1 H), 4.46 (q, J= 7.2 Hz, 2 H), 2.89 (s, 3 H), 1.57-1.51 (t, J 7.2 Hz, 3 H). MS (El) Calc?d for C,2H12N6C1 [M+H], 275; found, 275.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere;	Into a 5-L 4-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 6-chloro-9-ethyl-8-iodo-9H-purine (242 g, 784 mmol) , <strong>[1034924-06-5](2-methylpyrimidin-5-yl)boronic acid</strong> (108 g, 783 mmol), potassium carbonate (162 g, 1.17 mol) and Pd(dppf)Cl2-DCM (32 g, 39 mmol) in dioxane (2.4 L) and water (480 mL). The resulting solution was stirred overnight at 90 . The reaction mixture was cooled to room temperature, then extracted with 2 x 1.5 L of EtOAc. The organic extracts were combined, dried (MgSO4) and concentrated under vacuum. The residue was purified by chromatography on SiO2(5: 1: 1 petroleum ether/DCM/EtOAc) providing 6-chloro-9-ethyl-8- (2-methylpyrimidin-5-yl) -9H-purine (Intermediate I) .1H NMR (300 MHz, CDCl3) delta 9.12 (s, 2 H) , 8.80 (s, 1 H) , 4.46 (q, J 7.2 Hz, 2 H) , 2.89 (s, 3 H) , 1.57-1.51 (t, J 7.2 Hz, 3 H) . MS (EI) calc?d for C12H12N6Cl [M+H]+, 275 found, 275.

References: [1]Patent: WO2014/75392,2014,A1 .Location in patent: Page/Page column 66; 67; 68.
[2]Patent: WO2017/166104,2017,A1 .Location in patent: Page/Page column 57-58.

7
[ 7752-78-5 ]
[ 1034924-06-5 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; toluene; at -78℃; for 1h;Inert atmosphere;	Into a 1 0-L 4-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 5-bromo-2-iodopyrimidine (590 g, 2.07 mol) in THE (3 L). This was followed by dropwise addition of 1 M solution of dimethyl zinc (3.11 L, 3.11 mol) with stirring at 0°C. To this was added Pd(PPh3)4 (120 g, 104 mmol). The resulting solution was stirred for 3 h at 0°C, then quenched by the addition of 600 mL of aqueous NH4C1. The resultingsolution was extracted with 2 x 1.5 L of ethyl acetate. The organic extracts were combined, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was applied onto a silica gel colunm and eluted with ethyl acetate/petroleum ether (1:50) to provide 5-bromo-2-methylpyrimidine. Into a 1 0-L 4-neck round-bottom flask purged and maintained with an inert atmosphereof nitrogen was placed a solution of 5-bromo-2-methylpyrimidine (184 g, 1.06 mol) and B(iPrO) 3 (240 g, 1.28 mol) in THE/toluene (3/3 L). This was followed by the dropwise addition of a 2.5 M solution of n-BuLi (510 mL, 1.28 mol) with stirring at -78°C. The resulting solution was stirred for 1 hat -78°C, then quenched by the addition of 200 nit of aqueous NH4CI. The organic phase was dried and concentrated under vacuum. The aqueous phase was adjusted to pH4 with AcOH. The solid was collected by filtration and dried in an oven under reduced pressure providing (2-methylpyrimidin-5 -yl)boronic acid.
	With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; toluene; at -78℃; for 1h;Inert atmosphere;	Into a 10-L 4-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 5-bromo-2-methylpyrimidine (184 g, 1.06 mol) and B (i-PrO)3(240 g, 1.28 mol) in THF/toluene (3/3 L) . This was followed by the dropwise addition of a 2.5 M solution of n-BuLi (510 mL, 1.28 mol) with stirring at -78 . The resulting solution was stirred for 1 h at -78 , then quenched by the addition of 200 mL of aqueous NH4Cl. The organic phase was dried and concentrated under vacuum. The aqueous phase was adjusted to pH 4 with AcOH. The solid was collected by filtration and dried in an oven under reduced pressure providing (2-methylpyrimidin-5-yl) boronic acid.

References: [1]Patent: WO2014/75392,2014,A1 .Location in patent: Page/Page column 66; 67.
[2]Patent: WO2017/166104,2017,A1 .Location in patent: Page/Page column 57-58.

8
[ 1034924-06-5 ]
[ 1610720-03-0 ]