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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 : |
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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: |
* 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.
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]+. |
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. |
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. |
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]+. |
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)+. |
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). |
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. |
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. |
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)+. |
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]+. |
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]+. |
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]+. |
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)+ |
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 |
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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; triethylamine In ethanol; water at 120℃; Sealed tube; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With palladium diacetate; triethylamine In ethanol; water at 120℃; for 1.5h; Sealed tube; Microwave irradiation; |
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. |
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; |
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; |
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; |
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; |
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 |
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 |
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 |
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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 80℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol; water at 130℃; for 0.166667h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 80℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 80℃; for 48h; |
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; |
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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; toluene at 100℃; Inert atmosphere; |
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