[ CAS No. 942922-07-8 ] {[proInfo.proName]}

Name: 942922-07-8|2-(4-Methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine|97%
Brand: Ambeed
SKU: A689392
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Quality Control of [ 942922-07-8 ]

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Product Details of [ 942922-07-8 ]

CAS No. :	942922-07-8	MDL No. :	MFCD08669592
Formula :	C₁₅H₂₅BN₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LGIDGOSYDQTQDO-UHFFFAOYSA-N
M.W :	304.20	Pubchem ID :	16414228
Synonyms :

Safety of [ 942922-07-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 942922-07-8 ]

* 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.

Downstream synthetic route of [ 942922-07-8 ]

[ 942922-07-8 ] Synthesis Path-Downstream 1~33

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	Step 2: General procedure: To a solution of compound 1b-2 (1 g, 3.92 mmol) in DMF (20 mL) was added compound Pd(dppf)Cl2 (144 mg, 0.19 mmol), compound 1b.2 (1.2 g, 3.33 mmol) and potassium acetate (570 mg, 5.8 mmol), the mixture was stirred under argon atmosphere at 80° C. overnight. The reaction solution was concentrated and purified by combiflash to give compound 1b (400 mg, 31%). MS m/z (ESI): 304 [M+H]+.

2
[ 942922-07-8 ]
[ 947691-52-3 ]
7-methoxy-6-(2-methoxyethoxy)-4-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]cinnoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 140℃; for 0.0833333h; Microwave irradiation;	31 Example 31; Synthesis of 7-methoxy-6-(2-methoxyethoxy)-4-[2-(4-methylpiperazin- 1 -yl)pyrimidin-5- yl]cinnoline; [00286] Into a 5 mL microwave tube is added 4-bromo-7-methoxy-6-(2- methoxyethoxy)cinnoline (0.186 mmol), 2-(4-methylpiperazin-l-yl)-5-(4,4,5,5-tetramethyl-- l,3,2-dioxaborolan-2-yl)pyrimidine (145 mg, 0.478 mmol), bis(triphenylphosphine)palladium(H) chloride (26.9 mg, 0.0384 mmol), 2.00 M sodium carbonate in water (139 uL) and DME:Water:EtOH = 7:3:2 (7:3:2, 1,2-Dimethoxyethane:Water:Ethanol, 895 uL). The suspension is irradiated in a microwave at 300 W to 140 0C for 5.0 minutes. The reaction mixture is filtered through a celite plug and washed with methanol. The solution is concentrated under reduced pressure and the remaining residue is purified.

Reference： [1]Current Patent Assignee: AMGEN INC; ROCHE HOLDING AG - WO2007/100880, 2007, A1 Location in patent: Page/Page column 74

3
[ 879014-17-2 ]
[ 942922-07-8 ]
6,7-dimethoxy-4-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]cinnoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 140℃; for 0.0833333h; Microwave irradiation;	12 Example 12 Synthesis of 6.7-dimethoxy-4-r2-(4-methylpiperazin-l-yl')pyrimidin-5-vncinnoline [00187] Into a 5 mL microwave tube was added 4-bromo-6,7-dimethoxycinnoline(50.0 mg, 0.186 mmol), 2-(4-methylpiperazin-l-yl)-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyrimidine (145 mg, 0.478 mmol). bis(triphenylphosphine)palladium(II) chloride (26.9 mg, 0.0384 mmol), 2.00 M sodium carbonate in water (139 uL) and DME:Water:EtOH = 7:3:2 (7:3:2, l,2-Dimethoxyethane:Water:Ethanol, 895 uL). The cloudy, brown suspension was irradiated in a microwave at 300 W to 140 0C for 5.(3 minutes. The reaction mixture was filtered through a celite plug and washed with methanol. The solution was concentrated under reduced pressure and the remaining residue was purified by rotary chromatography using a gradient elution going from 100% chloroform to 10% methanol in chloroform to provide 64 mg of 6,7-dimethoxy-4-[2-(4-methylpiperazin-l- yl)pyrimidin-5-yl]cinnoline.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2007/98169, 2007, A1 Location in patent: Page/Page column 60-61

4
[ 942922-07-8 ]
[ 834888-64-1 ]
[ 1092367-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine; N-(4-methoxybenzyl)-2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide With sodium carbonate In tetrahydrofuran; water at 160℃; for 1h; Microwave irradiation; Stage #2: With trifluorormethanesulfonic acid; trifluoroacetic acid In dichloromethane at 20℃; for 3h;	19 iY-(2-chloro-6-methylphenyl)-2-(2-methyl-2'-(4-methylpiperazin-l-yl)-4,5'- bipyrimidin-6-ylamino)thiazole-5-carboxamide4A mixture of 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6- methylphenyl)-N-(4-methoxybenzyl)thiazole-5-carboxamide (46 mg, 0.089 mmol), 2-(4-methylpiperazin-l-yl)-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine(35 mg, 0.12 mmol), Pd(PPh3)4 (30 mg, 0.026 mmol), sodium carbonate (26 mg, 0.25 mmol) in THF (3.0 mL) and water (0.30 mL) was microwave heated at 160 0C for 1 h.The solvent was removed and the residue was purified by silica gel chromatography.The product was dissolved in 50% TFA in DCM (3 mL) and triflic acid (0.2 mL).The reaction mixture was stirred for 3 h at rt, diluted with EtOAc, washed with sat. sodium bicarbonate, brine, dried over sodium sulfate and the solvent was removed. The residue was purified by preparative HPLC (ACν/ 0.1 % TFA in water) and lyophilized to yield the TFA salt of the title compound as a slightly yellow fluffy solid.1H-NMR (400 MHz, d6-DMSO) δ 12.12 (br s, IH), 9.99 (s, IH), 9.83 (br s, IH), 9.04(s, 2H), 8.32 (s, IH), 7.41 (dd, J = 1.6 Hz, 7.6 Hz, IH), 7.32-7.26 (m, 3H), 4.83 (d, J = 14.0 Hz, 2H), 3.56-3.35 (m, 4H), 3.12 (t, 2H), 2.86 (s, 3H), 2.65 (s, 3H), 2.25 (s,3H); MS (m/z): 536.2 [M+l]+.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH - WO2008/150446, 2008, A1 Location in patent: Page/Page column 40

5
[ 141302-36-5 ]
[ 73183-34-3 ]
[ 942922-07-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-bromo-2-(4-methylpiperazin-1-yl)pyrimidine; bis(pinacol)diborane With potassium acetate In 1,4-dioxane for 0.25h; Stage #2: With tricyclohexylphosphine In 1,4-dioxane at 80℃; for 2.25h;	26.c A solution of 5-bromo-2-(4-methylpiperazin-1-yl)pyrimidine (0.25 g, 0.98 mmol), bispinacolatodiboron (0.27 g, 1.07 mmol) and KOAc (0.12 g, 1.46 mmol) in 1 ,4- dioxane (5.0 ml.) was degassed by flushing with nitrogen for 15 min. Tricyclohexylphosphine (0.027 g, 0.096 mmol) and tris(dibenzyledineacetone) dipalladium (0) (0.044 g, 0.048 mmol) was then added to the reaction mixture, which was again degassed by nitrogen for 15 min. The resulting reaction mixture was heated to 8O0C for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was filtered through celite bed and the filtrate was concentrated to get the crude residue that was carried forward to the next step without further purification. MS: 305.20 (M+H)+.

Reference： [1]Current Patent Assignee: SPERO THERAPEUTICS INC - WO2009/74812, 2009, A1 Location in patent: Page/Page column 68

6
[ 942922-07-8 ]
[ 1160789-92-3 ]
[ 1160790-76-0 ]

Yield	Reaction Conditions	Operation in experiment
18%	Stage #1: 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine; 1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea With potassium phosphate In water; N,N-dimethyl-formamide for 0.25h; Stage #2: In water; N,N-dimethyl-formamide at 100℃; for 2.25h;	57 A solution of 1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea (0.13 g, 0.41 mmol), ' 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidine M-A (0.25 g, 0.82 mmol) and K3PO4 (0.173 g, 0.82 mmol) in DMF-H2O (5.0 ml_, 4:1) was degassed by flushing with nitrogen for 15 min. Dichlorobis(triphenylphosphine)- palladium(ll) (0.057 g, 0.05 mmol) was then added to the reaction mixture followed by degassing with nitrogen for another 15 min. The resulting reaction mixture was then heated to 100°C for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to room temperature and poured onto ice-cold water followed by extraction with EtOAc (2 x 50 ml_). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was then purified over silica gel (100-200 M, 4.20% MeOH-DCM) to obtain the desired product (0.03 g, 18%). 1H-NMR (400 MHz, DMSO-d6): δ 1.08 (t, J= 7.20 Hz, 3H), 2.26 (s, 3H), 2.43 (br s, 4H), 3.20 (quintet, J= 7.20 Hz, 2H), 3.80 (br s, 4H), 6.72 (br s, 1H), 7.75 (d, J= 6.80 Hz, 1 H), 7.91 (d, J= 10.40 Hz, 1 H), 8.60 (s, 2H) and 10.75 (br s, 1H). MS: 416.28 (M+H)+. Qualitative HPLC Purity (Acquity BEH C-18, 100 x 2.1 mm, 229 nm): 96.97% (Rt = 5.04 min).

Reference： [1]Current Patent Assignee: SPERO THERAPEUTICS INC - WO2009/74812, 2009, A1 Location in patent: Page/Page column 69

7
[ 669050-69-5 ]
[ 942922-07-8 ]
[ 1168723-08-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 125℃; for 2h;Microwave irradiation;	A mixture of lH-indazole-6-carbaldehyde (50 mg, 0.18 mmol), 2-(4- Methylpiperazin-l-yl)pyrimidine-5-boronic acid pinacol ester (70 mg, 0.22 mmol), Pd(PPh3)4 (13 mg, 0.018 mmol) and 2M Na2CO3 (0.10 mL, 0.22 mmol) in DME/H2O/EtOH (1.4 mL/0.4 mL/0.2 mL) was sealed and heated with stirring under microwave irradiation at 125 0C for 120 min. The crude reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel using MeOH (5% to 10 %) in DCM as the eluent to provide the title compound as a pale yellow solid (47 mg, 80 %). 1H NMR (400 MHz, CD3OD) delta ppm 10.12 (s, 1 H), 8.91 (s, 2 H), 8.14 (s, 1 H), 8.09 (d, J= 8.6 Hz, 1 H), 7.74 (d, J= 8.4 Hz, 1 H), 3.94 (t, J= 4.5 Hz, 4 H), 2.56 (t, J= 4.9 Hz, 4 H), 2.37 (s, 3 H); MS ESI 323.1 (100) [M + H]+, calcd for [Ci7H18N6O + H]+ 323.2.

Reference： [1]Patent: WO2009/79767,2009,A1 .Location in patent: Page/Page column 207

8
[ 942922-07-8 ]
[ 1346703-22-7 ]
[ 1346703-26-1 ]

Yield	Reaction Conditions	Operation in experiment
14.83%	With sodium carbonate In 1,2-dimethoxyethane; water at 150℃; for 0.5h; Microwave irradiation;	46 Example 46l-cyclopent l-N-((4,6-dimethyl-2-oxo-l,2-dihydropyridin-3-yl)methyl)-6-(2-(4-methy]piperazin- l-yl)pyrimidin-5-yl)-lTo a 2 mL microwave vial were added 6-bromo- l-cyclopentyl-N-[(4,6-dimethyl-2-oxo-l,2-dihydro- 3-pyridinyl)methyl]-lH-indazole-4-carboxamide (150 mg, 0.338 mmol), 2-(4-methyl- 1 -piperazinyl)- 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine (134 mg, 0.440 mmol), Na2C03 (108 mg, 1.015 mmol), PdCl2(dppf)-CH2Cl2 adduct (27.6 mg, 0.034 mmol), 1 ,2-Dimethoxy ethane (1269 μ) and water (423 μ). The contents were irradiated in a microwave reactor at 150 °C for 30 min. The reaction solution was filtered through a Whatman 0.45μ1 Teflon syringless filter device and diluted with DMSO (6 mL). The DMSO solution was purified by HPLC reverse phase chromatography (phenomenex Gemini-NX, 30x100 5μ column, 5-30% acetonitrile/water 0.01% formic acid, 8 min gradient). The fractions containing the desired product were concentrated to dryness using a Genovac HT-4 instrument at 40 °C. The title compound was obtained as a pale cream colored foam (28 mg, 14.83 % yield). ¾ NMR (400 MHz, CHLOROFORM-δ) δ 8.62 (s, 2H), 8.39 (s, 1H), 7.99 (t, J = 5.56 Hz, 1H), 7.71 (s, 1H), 7.57 (s, 1H), 5.98 (s, 1H), 5.03 (quin, J = 7.14 Hz, 1H), 4.66 (d, J = 5.81 Hz, 2H), 3.97 (br. s., 4H), 2.64 (br. s., 4H), 2.44 (s, 6H), 2.12 - 2.25 (m, 7H), 1.89 - 2.07 (m, 2H), 1.67 - 1.85 (m, 2H). LCMS(ES) [M+H]+ 541.5.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/140325, 2011, A1 Location in patent: Page/Page column 77

9
[ 942922-07-8 ]
[ 1417184-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane	282 7-[2-(4-Methyl-piperazin-1-yl)-pyrimidin-5-yl]-2-(2-quinolin-2-yl-ethyl)-2,3-dihydro-isoindol-1-one Example 282 7-[2-(4-Methyl-piperazin-1-yl)-pyrimidin-5-yl]-2-(2-quinolin-2-yl-ethyl)-2,3-dihydro-isoindol-1-one The title compound was prepared in analogy to the process described in Example 281 using 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (30.4 mg, 0.1 mmol) dissolved in dioxane (0.3 mL) instead of 5-cyanothiophen-2-ylboronic acid (15.3 mg, 0.1 mmol) dissolved in dioxane (0.3 mL). Yield: 12.4 mg, 32%. 1H NMR (400 MHz, DMSO-d6/D2O) δ ppm 8.41 (s, 1H) 8.29 (d, J=8.54 Hz, 1H) 7.86-7.95 (m, 2H) 7.69-7.75 (m, 1H) 7.60-7.65 (m, 1H) 7.52-7.58 (m, 3H) 7.47-7.50 (m, 1H) 7.38 (d, J=7.63 Hz, 1H) 4.52 (s, 2H) 3.98 (t, J=7.17 Hz, 2H) 3.76-3.80 (m, 4H) 3.28 (t, J=7.02 Hz, 2H) 2.37-2.42 (m, 4H) 2.21-2.24 (m, 3H); MS (ESI) m/z 465 (M+H)+.

Reference： [1]Current Patent Assignee: ABBVIE INC - US2013/5705, 2013, A1

10
[ 24634-04-6 ]
[ 942922-07-8 ]
5-methyl-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-2H-isoquinolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; ethanol; water at 100℃; for 1h; Inert atmosphere; Microwave irradiation;	5-Methyl-3-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-2H-isoquinolin-1-one (IQ-025) 5-Methyl-3-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-2H-isoquinolin-1-one (IQ-025) 3-Chloro-5-methyl-2H-isoquinolin-1-one (50 mg, 0.26 mmol), 2-(4-methylpiperazin-1-yl)pyrimidine-5-boronic acid pinacol ester (118 mg, 0.39 mmol), K2CO3 (73 mg, 0.52 mmol) and Pd(dppf)Cl2 (10 mg, 0.013 mmol) in DME/EtOH/H2O 4:0.5:1 (2.75 mL) were added to a microwave vial and the reaction mixture purged with N2 for 10 min. The reaction mixture was irradiated using a microwave reactor (300 W, 100° C., 60 min). The reaction mixture was filtered through celite and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with CH2Cl2 and increasing the polarity to 50% MeOH/CH2Cl2. The crude material was trituared with MeOH and washed with isohexane to afford 5-methyl-3-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-2H-isoquinolin-1-one as an off-white solid (28 mg, 32%). AnalpH2_MeOH_QC(1): Rt 4.97 min; m/z 336 [M+1]+.

Reference： [1]Current Patent Assignee: UNIVERSITY OF LONDON - US2015/99732, 2015, A1 Location in patent: Paragraph 1494-1495

11
[ 942922-07-8 ]
3-bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(1H-tetrazol-5-yl)phenyl]-L-phenylalaninamide [ No CAS ]
N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-N-[4-(1H-tetrazol-5-yl)phenyl]-L-phenylalaninamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; dimethyl sulfoxide at 110℃; for 2h; Microwave irradiation;	105A Example 105A N-alpha-[(trans-4-[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-N-[4-(1H-tetrazol-5-yl)phenyl]-L-phenylalaninamide Example 105A N-alpha-[(trans-4-[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-N-[4-(1H-tetrazol-5-yl)phenyl]-L-phenylalaninamide 3-Bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(1H-tetrazol-5-yl)phenyl]-L-phenylalaninamide (184 mg, 0.29 mmol) and 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (98 mg, 0.32 mmol) were dissolved in dimethyl sulphoxide (2 ml), and tetrakis(triphenylphosphine)palladium(0) (34 mg, 29 μmol), sodium carbonate (93 mg, 0.88 mmol) and water (0.44 ml, 25 mmol) were added. The reaction mixture was stirred at 110° C. in a microwave (Biotage Initiator) for 120 min, cooled, filtered and purified by chromatography via HPLC (Method 10). This gave 86 mg (40% of theory) of the title compound. LC-MS (Method 4): Rt=0.92 min; MS (ESIpos): m/z=724.3 [M+H]+.

Reference： [1]Current Patent Assignee: BAYER AG - US2016/244437, 2016, A1 Location in patent: Paragraph 1099; 1100; 1101

12
[ 942922-07-8 ]
3-bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(3-chloro-4H-1,2,4-triazol-5-yl)phenyl]-L-phenylalaninamide [ No CAS ]
N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(3-chloro-4H-1,2,4-triazol-5-yl)phenyl]-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-L-phenylalaninamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; dimethyl sulfoxide at 110℃; for 2h; Microwave irradiation;	127A Example 127A N-alpha-[(trans-4-[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(3-chloro-4H-1,2,4-triazol-5-yl)phenyl]-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-L-phenylalaninamide Example 127A N-alpha-[(trans-4-[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(3-chloro-4H-1,2,4-triazol-5-yl)phenyl]-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-L-phenylalaninamide 3-Bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(3-chloro-4H-1,2,4-triazol-5-yl)phenyl]-L-phenylalaninamide (150 mg, 0.23 mmol) and 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (104 mg, 0.34 mmol) were dissolved in dimethyl sulphoxide (2 ml), and tetrakis(triphenylphosphine)palladium(0) (26 mg, 23 μmol), sodium carbonate (72 mg, 0.68 mmol) and water (0.34 ml, 19 mmol) were added. The reaction mixture was stirred at 110° C. in a microwave (Biotage Initiator) for 120 min, cooled, filtered and purified by chromatography via HPLC (Method 11). This gave 52 mg (30% of theory) of the title compound. LC-MS (Method 5): Rt=0.85 min; MS (ESIpos): m/z=757.6 [M+H]+.

Reference： [1]Current Patent Assignee: BAYER AG - US2016/244437, 2016, A1 Location in patent: Paragraph 1166; 1167; 1168

13
[ 942922-07-8 ]
3-bromo-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine [ No CAS ]
8-[(2,6-difluorobenzyl)oxy]-2-methyl-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 80℃;	6 8-[(2,6-Difluorobenzyl)oxy]-2-methyl-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]imidazo[1,2-a]pyridine 125 mg (0.35 mmol) of 3-bromo-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine (Example 19A), 118 mg (0.39 mmol) of 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine and 119 mg (1.42 mmol) of sodium bicarbonate were initially charged with 14 mg (0.02 mmol) of 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) chloride/dichloromethane complex, and a degassed 3:1 mixture of 1,2-dimethoxyethane and water was added. The mixture was stirred overnight at 80° C. The reaction solution was diluted with acetonitrile/water, filtered through a Millipore filter and purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The product fractions were concentrated and the residue was taken up in dichloromethane and washed twice with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted two more times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered, concentrated and lyophilized. This gave 77 mg of the target compound (48% of theory). LC-MS (Method 16): Rt=0.46 min MS (ESpos): m/z=451 (M+H)+

Reference： [1]Current Patent Assignee: BAYER AG - US2017/304278, 2017, A1 Location in patent: Paragraph 0730; 0731; 0732; 0733

14
[ 64-18-6 ]
[ 942922-07-8 ]
7-bromo-N-(3-chloro-4-methoxyphenyl)quinolin-4-amine [ No CAS ]
N-(3-chloro-4-methoxyphenyl)-7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)quinolin-4-amine formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine; 7-bromo-N-(3-chloro-4-methoxyphenyl)quinolin-4-amine With palladium diacetate; triethylamine In ethanol; water at 120℃; Sealed tube; Microwave irradiation; Stage #2: formic acid In water; acetonitrile

Reference： [1]Mehta, Naimee; Ferrins, Lori; Leed, Susan E.; Sciotti, Richard J.; Pollastri, Michael P. [ACS Infectious Diseases, 2018, vol. 4, # 4, p. 577 - 591]

15
[ 64-18-6 ]
[ 942922-07-8 ]
N-(1H-benzo[d][1,2,3]triazol-5-yl)-7-bromoquinolin-4-amine [ No CAS ]
N-(1H-benzo[d][1,2,3]triazol-5-yl)-7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)quinolin-4-amine formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine; N-(1H-benzo[d][1,2,3]triazol-5-yl)-7-bromoquinolin-4-amine With palladium diacetate; triethylamine In ethanol; water at 120℃; Sealed tube; Microwave irradiation; Stage #2: formic acid In water; acetonitrile

Reference： [1]Mehta, Naimee; Ferrins, Lori; Leed, Susan E.; Sciotti, Richard J.; Pollastri, Michael P. [ACS Infectious Diseases, 2018, vol. 4, # 4, p. 577 - 591]

16
[ 942922-07-8 ]
7-bromo-N-(pyrazin-2-yl)quinolin-4-amine [ No CAS ]
7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-N-(pyrazin-2-yl)quinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; triethylamine In ethanol; water at 120℃; Sealed tube; Microwave irradiation;

Reference： [1]Mehta, Naimee; Ferrins, Lori; Leed, Susan E.; Sciotti, Richard J.; Pollastri, Michael P. [ACS Infectious Diseases, 2018, vol. 4, # 4, p. 577 - 591]

17
[ 942922-07-8 ]
7-bromo-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)quinolin-4-amine [ No CAS ]
N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)quinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With palladium diacetate; triethylamine In ethanol; water at 120℃; for 1.5h; Sealed tube; Microwave irradiation;

Reference： [1]Mehta, Naimee; Ferrins, Lori; Leed, Susan E.; Sciotti, Richard J.; Pollastri, Michael P. [ACS Infectious Diseases, 2018, vol. 4, # 4, p. 577 - 591]

18
[ 942922-07-8 ]
tert-butyl 5-chloro-3-iodo-1H-pyrazolo[4,3-d]pyrimidine-1-carboxylate [ No CAS ]
tert-butyl 5-chloro-3-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-1H-pyrazolo[4,3-d]pyrimidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 50℃; for 16h; Sealed tube; Inert atmosphere;	105.4 Step 4. tert-Butyl 5-chloro-3-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-1H-pyrazolo[4,3-d]pyrimidine-1-carboxylate To a screw-cap vial equipped with a magnetic stir bar was added tert-butyl 5-chloro-3-iodo-1H-pyrazolo[4,3-d]pyrimidine-1-carboxylate (1026.0 mg, 2.70 mmol), 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (816.5 mg, 2.68 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (440.2 mg, 0.539 mmol) and cesium carbonate (2693 mg, 8.27 mmol). The vial was sealed with a Teflon-lined septum, evacuated and backfilled with nitrogen (this process was repeated a total of three times). 1,4-Dioxane (12.0 ml) was added, followed by water (4.0 ml). The reaction was stirred at 50° C. for 16 h. After cooling to room temperature, the mixture was diluted with CH2Cl2, and washed with brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified on silica gel (40 g, 0-100% EtOAc in hexanes then 10% MeOH in CH2Cl2) to give the desired product as a yellow solid (877.3 mg, 76%). LCMS calculated for C19H24ClN8O2 (M+H)+ m/z=431.2; found 431.1.

Reference： [1]Current Patent Assignee: INCYTE CORP - US2018/72741, 2018, A1 Location in patent: Paragraph 0813-0814; 0867-0868

19
[ 942922-07-8 ]
7-bromo-6-methyl-N-(pyrazin-2-yl)quinolin-4-amine [ No CAS ]
6-methyl-7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-N-(pyrazin-2-yl)quinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane at 130℃; for 0.166667h; Microwave irradiation;

Reference： [1]Bachovchin, Kelly A.; Sharma, Amrita; Bag, Seema; Klug, Dana M.; Schneider, Katherine M.; Singh, Baljinder; Jalani, Hitesh B.; Buskes, Melissa J.; Mehta, Naimee; Tanghe, Scott; Momper, Jeremiah D.; Sciotti, Richard J.; Rodriguez, Ana; Mensa-Wilmot, Kojo; Pollastri, Michael P.; Ferrins, Lori [Journal of Medicinal Chemistry, 2019, vol. 62, # 2, p. 665 - 687]

20
[ 942922-07-8 ]
7-bromo-8-methyl-N-(pyrazin-2-yl)quinolin-4-amine [ No CAS ]
8-methyl-7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-N-(pyrazin-2-yl)quinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane at 130℃; for 0.166667h; Microwave irradiation;

21
[ 942922-07-8 ]
4-bromo-N-(3-chloro-4-methoxyphenyl)-2-hydroxybenzamide [ No CAS ]
N-(3-chloro-4-methoxyphenyl)-2-hydroxy-4-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In N,N-dimethyl-formamide Heating; Inert atmosphere;

22
[ 956268-33-0 ]
[ 942922-07-8 ]
7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)quinolin-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water Heating;

23
[ 942922-07-8 ]
4-chloro-7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / Heating 2: trichlorophosphate / neat (no solvent) / Reflux

24
[ 942922-07-8 ]
7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-N-(1-methylpiperidin-4-yl)quinolin-4-amine triformate salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / Heating 2: trichlorophosphate / neat (no solvent) / Reflux 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium <i>tert</i>-butylate; XPhos / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere

25
[ 942922-07-8 ]
7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-N-(2-(pyrrolidin-1-yl)ethyl)quinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / Heating 2: trichlorophosphate / neat (no solvent) / Reflux 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium <i>tert</i>-butylate; XPhos / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere

26
[ 64-18-6 ]
[ 942922-07-8 ]
7-bromo-N-cyclohexylquinolin-4-amine [ No CAS ]
N-cyclohexyl-7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)quinolin-4-amine monoformate salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	Stage #1: 2-(4-methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine; 7-bromo-N-cyclohexylquinolin-4-amine With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 130℃; for 0.5h; Microwave irradiation; Stage #2: formic acid

27
[ 942922-07-8 ]
N1-(7-bromoquinolin-4-yl)-N4,N4-dimethylcyclohexane-1,4-diamine [ No CAS ]
N1,N1-dimethyl-N4-(7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)quinolin-4-yl)cyclohexane-1,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane; water at 80℃; for 48h;

28
[ 942922-07-8 ]
7-bromo-N-(tetrahydro-2H-pyran-4-yl)quinolin-4-amine [ No CAS ]
7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-N-(tetrahydro-2H-pyran-4-yl)quinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In ethanol; water at 130℃; for 0.166667h; Microwave irradiation;

29
[ 942922-07-8 ]
7-bromo-N-((tetrahydro-2H-pyran-4-yl)methyl)quinolin-4-amine [ No CAS ]
7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)quinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane; water at 80℃; for 18h;

30
[ 942922-07-8 ]
(1R,2R)-2-((7-bromoquinolin-4-yl)amino)cyclohexan-1-ol [ No CAS ]
(1R,2R)-2-((7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)quinolin-4-yl)amino)cyclohexan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane; water at 80℃; for 48h;

31
[ 942922-07-8 ]
C₁₄H₁₁BrN₄ [ No CAS ]
(E)-1-methyl-7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-N-(pyrazin-2-yl)quinolin-4(1H)-imine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 130℃; for 0.5h; Inert atmosphere; Microwave irradiation;

Reference： [1]Ackermann, Jasmin; Bachovchin, Kelly A.; Bag, Seema; Bernatchez, Jean A.; Buskes, Melissa J.; Calvet, Claudia M.; Campbell, Robert F.; Erath, Jessey; Ferrins, Lori; Jalani, Hitesh B.; Klug, Dana M.; Leed, Susan E.; McCall, Laura-Isobel; McKerrow, James; Penn, Erica C.; Pollastri, Michael P.; Rodriguez, Ana; Roncal, Norma E.; Sciotti, Richard J.; Silva, Everton M.; Singh, Baljinder; Siqueira-Neto, Jair L.; Souza, Julia M.; Thomas, Diane [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 3, p. 249 - 257]

32
[ 942922-07-8 ]
7-bromo-N-(5-methylpyrazin-2-yl)quinolin-4-amine [ No CAS ]
7-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)-N-(5-methylpyrazin-2-yl)quinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; potassium carbonate In 1,4-dioxane; water at 130℃; for 0.333333h; Inert atmosphere; Microwave irradiation;

Reference： [1]Bachovchin, Kelly A.; Bag, Seema; Buskes, Melissa J.; Caffrey, Conor R.; Campbell, Robert F.; Clements, Monica; El-Sakkary, Nelly; Ferrins, Lori; Jalani, Hitesh B.; Klug, Dana M.; Leonard, Allison; Pollastri, Michael P.; Sciotti, Richard J.; Singh, Baljinder [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 3, p. 258 - 265]

33
[ 942922-07-8 ]
ethyl 1-[1-{5-chloro-2-[(trifluoromethanesulfonyl)oxy]phenyl}piperidin-3-yl]-5-(difluoromethyl)-1H-pyrazole-4-carboxylate [ No CAS ]
ethyl 1-[1-{5-chloro-2-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]phenyl}piperidin-3-yl]-5-(difluoromethyl)-1H-pyrazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; toluene at 100℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: BAYER AG - WO2022/122913, 2022, A1 Location in patent: Page/Page column 190; 191

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P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 942922-07-8 ] {[proInfo.proName]}

Quality Control of [ 942922-07-8 ]

Related Doc. of [ 942922-07-8 ]

Product Details of [ 942922-07-8 ]

Safety of [ 942922-07-8 ]

Application In Synthesis of [ 942922-07-8 ]

[ 942922-07-8 ] Synthesis Path-Downstream 1~33

Related Functional Groups of [ 942922-07-8 ]

Organoboron

Esters

Related Parent Nucleus of [ 942922-07-8 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 942922-07-8 ]

Related Parent Nucleus of
[ 942922-07-8 ]