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[ CAS No. 1032759-30-0 ] {[proInfo.proName]}

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Chemical Structure| 1032759-30-0
Chemical Structure| 1032759-30-0
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Product Details of [ 1032759-30-0 ]

CAS No. :1032759-30-0 MDL No. :MFCD07368238
Formula : C12H20BN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RMPRVJCNMPFBCX-UHFFFAOYSA-N
M.W : 249.12 Pubchem ID :16414215
Synonyms :

Calculated chemistry of [ 1032759-30-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.67
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 72.71
TPSA : 47.48 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 0.84
Log Po/w (MLOGP) : 0.26
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.721 mg/ml ; 0.00289 mol/l
Class : Soluble
Log S (Ali) : -2.26
Solubility : 1.37 mg/ml ; 0.00549 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.37
Solubility : 0.107 mg/ml ; 0.000429 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.01

Safety of [ 1032759-30-0 ]

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 [ 1032759-30-0 ]

* 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 [ 1032759-30-0 ]

[ 1032759-30-0 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 1032759-30-0 ]
  • [ 1034303-30-4 ]
  • [ 1034303-40-6 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate;[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; In 1,4-dioxane; at 60.0℃; for 16h; Compound H .21A mixture of [C2] (100mg, 0.29mmol), [1 ,3-bis(2,6.diisopropylphenyl)imidazol-2-ylidene](3- chloropyridyl)palladium(ll) dichloride (PEPPSI) (5mg, 0.01 mmol), 2- dimethylaminopyrimidine-5-boronic acid pinacol ester (78mg, 0.31 mmol) and potassium carbonate (119mg, O.deltadeltammol) in 1 ,4-dioxane (5ml) under argon, was heated at 6O0C for 16 hours. The mixture was evaporated and the residue subjected to column chromatography over silica, eluting with an ethyl acetate/heptane gradient to give 5-(2-dimethylamino- pyrimidin-5-yl)-1-(2-fluoro-phenyl)-4-formyl-1 H-pyrazole-3-carboxylic acid cyclohexylamide(100mg, 0.23mmol, 80%).LCMS: RT = 2.779min. (M+H)+ = 437.
  • 2
  • [ 1032759-30-0 ]
  • [ 1206195-35-8 ]
  • [ 1206194-28-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; at 90.0℃; <strong>[1032759-30-0]2-dimethylamino-pyrimidine-5-boronic acid pinacol ester</strong> (2eq.) was added to a solution of N-[4-(5-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamino)-phenyl]-acetamide in dioxan/water (5:1) (or EtOH). K2CO3 (2 eq.) and PdC^dppf (cat.) were added to the mixture. The resulting mixture was heated in an oil bath at 900C for 4 to 16 h until the reaction went to completion (monitored by LCMS). Water was added and the mixture was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous MgStheta4 and evaporated in vacuo to yield the crude product. The crude product was then purified by preparative HPLC.
  • 3
  • [ 1032759-30-0 ]
  • [ 1221165-86-1 ]
  • [ 1221165-87-2 ]
YieldReaction ConditionsOperation in experiment
65% With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 120.0℃; for 0.25h;Microwaves; A mixture of 3A (70mg, 0.20 mmol), <strong>[1032759-30-0]2-(dimethylamino)pyrimidine-5-boronic acid pinacol ester</strong>, (98mg, 0.39 mmol), Pd(dppf)CI2-CH2Cl2 (16mg, 0.02 mmol), K3PO4 (125mg, 0.59 mmol) in 3:1 DME-H2O (2 ml_) were microwaved at 120 C for 15 min. The reaction was diluted with EtOAc and washed with water (3x). The organic layer were dried over Na2SO4, concentrated and chromatographed (2% of NH3-MeOH/DCM) to give 3B (50mg, 65%) as a yellow solid. LCMS m/z 399 (MH+).
  • 4
  • [ 944401-95-0 ]
  • [ 1032759-30-0 ]
  • [ 1254697-45-4 ]
  • 5
  • [ 38696-21-8 ]
  • [ 73183-34-3 ]
  • [ 1032759-30-0 ]
YieldReaction ConditionsOperation in experiment
60% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; 1,2-dimethoxyethane; at 150.0℃; for 0.25h;Inert atmosphere; Microwave irradiation; A mixture of 5-bromo-N,N-dimethylpyrimidin-2-amine (0.966 g, 4.78 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (1.46 g, 5.74 mmol), PdCl2dppf(DCM) (0.114 g, 0.14 mmol) and KOAc (1.407 g, 14.34 mmol) were placed under Ar in a 20 mL microwave flask. Anhydrous 1,2-dimethoxyethane (16 mL) was added and the flask was irradiated at 150 oC for 15 minutes. The reaction was filtered through celite, concentrated and slurried in EtOAc. The reaction was filtered through celite again and the organics were concentrated and purified by column chromatography 0 to 30 % EtOAC in Hexanes. The material was isolated as a light teal solid (0.718 g, 60 % yield). 1H NMR (400 MHz, CDCl3) delta 8.59 (s, 2H), 3.21 (s, 6H), 1.31 (s, 12H).13C NMR (100 MHz, CDCl3) delta 164.1, 83.7, 77.4, 37.2, 25.2, 24.9. HRMS (EI+) m/z calculated for C12H12BN3O2 [M+H]+: 250.1721, found: 250.17189.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100.0℃; for 12h;Inert atmosphere; PdCl2(dppf)-CH2Cl2 adduct (323 mg, 0.396 mmol) was added to a solution of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (1207 mg, 4.75 mmol), 5-bromo- N,N-dimethylpyrimidin-2-amine (800 mg, 3.96 mmol) and potassium acetate (1 166 mg, 1 1 .88 mmol) in 1 ,4-dioxane (10 ml_) at room temperature under an atmosphere of nitrogen. The resulting solution was stirred at 100 C for 12 hr. The reaction was filtered and the filtrate was concentrated to afford crude product.
0.6 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100.0℃; for 4.5h; A mixture of 0.5 g (2.48 mmol) 5-bromo-N,N-dimethyl-pyrimidin-2-amine, 0.8 g (3.24 mmol) bis(pinacolato)diborone, 0.6 g (6.38 mmol) KOAc, 0.2 g (0.25 mmol) (0358) Pd(dppf)CI2 * DCM and dioxane is heated to 100C for 4.5 h. After cooling to RT, the reaction mixture is filtered through a pad of Celite and evorated, water is added and the mixture is extracted with EtOAc. The organic phases are pooled, dried and evaporated The crude product is purified by FC. (0359) Yield: 0.6 g (96%), ESI-MS: m/z = 250 (M+H)+, Rt(HPLC): 0.22 min (HPLC-A)
  • 6
  • [ 1032759-30-0 ]
  • [ 1310584-13-4 ]
  • [ 1310584-20-3 ]
YieldReaction ConditionsOperation in experiment
68% With potassium phosphate; (chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II)); In tetrahydrofuran; water; at 45.0℃; for 24h;Inert atmosphere; General procedure: Compound 4 0.05 mmol (1 equiv) and 0.15 mmol K3PO4 were placed in a Schlenk tube and dissolved in 16 ml of a degassed THF/H2O mixture (5:3). The solution was purged with N2 for further 30 min, followed by the addition of 0.15 mmol of the corresponding boronic acid (or ester, respectively) and 10 mol % of precatalyst 5. The Schlenk tube was sealed, and the reaction mixture was heated to 45 C and stirred for 24 h (unless not denoted differently for the specific reaction) under N2. After completion (TLC and ESI-MS monitoring), the reaction mixture was evaporated to dryness, the residue was dissolved in 30 ml of CHCl3 and washed twice with 10 ml of water. The organic phase was then dried over anhydrous Na2SO4, evaporated to dryness and purified via column chromatography (silica/varying eluents).
YieldReaction ConditionsOperation in experiment
26% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 85.0℃;Inert atmosphere; General procedure: Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107)[0334]To a solution of compound 0601-107 (2.5 g, 11.6 mmol) and bis(pinacolato)diboron (4.4 g, 17.5 mmol) in dioxane (100 mL) was added potassium acetate (3.4 g, 35 mmol) and PdCl2(dppf)2 (0.95 g, 1.1 mmol). The mixture was degassed with nitrogen and heated at 85 C. for overnight. The reaction mixture was concentrated under reduced pressure to afford the crude product, which purified by column chromatography (ethyl acetate in petroleum ether, 15% v/v) to give the compound 0602-107 (1.55 g, 51%) as a pink solid. LCMS: 262 [M+1]+. 1H NMR (400 MHz, DMSO-d6) delta 1.29 (s, 12H), 2.03 (s, 3H), 7.30 (s, 1H), 7.31 (d, J=2.0 Hz 1H), 7.73 (d, J=2.0 Hz, 1H), 7.89 (d, J=1.6 Hz, 1H), 9.93 (s, 1H).
26% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; at 85.0℃;Inert atmosphere; General procedure: Compound in dioxane (100mL) 0601-107 (2.5g, 11.6mmol) and a solution of bis (pinacolato) diboron (4.4 g, 17.5 mmol), potassium acetate (3.4 g, 35 mmol) and and PdCl2 (dppf) 2 ( 0.95g, 1.1mmol) was added. The mixture was degassed with nitrogen and heated overnight at 85 C.. The reaction mixture was concentrated under reduced pressure to give the crude product, which was purified by column chromatography (petroleum ether in ethyl acetate, 15% v / v) to give the compound 0602-107 as a pink solid obtained (1.55 g, 51%).
  • 8
  • [ 1032759-30-0 ]
  • [ 1332450-86-8 ]
  • [ 1332447-93-4 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 95.0℃; for 0.5h;Inert atmosphere; Example No. 31; Preparation of Compound No. 31[0328] A solution of 5-(2-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro- lH-pyrido[4,3- b]indole (100 mg, 0.282 mmol), <strong>[1032759-30-0]2-(dimethylamino)pyrimidine-5-boronic acid pinacol ester</strong> (105.5 mg, 0.423 mmol) and potassium phosphate (149.7 mg, 0.706 mmol) in DMF (4 mL) - water (1 mL) was purged with nitrogen followed by addition ofdichlorobis(triphenylphosphine) palladium (II) (9.91 mg, 5 mol %). The reaction mixture was heated at 95 C for 30 min under nitrogen atmosphere. The reaction mixture was diluted with water, extracted with EtOAc, the organic layer dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain crude which was purified by reverse phase HPLC to yield 9 mg of the title compound. 1H NMR (TFA salt, CD3OD) d (ppm): 8.03 (s, 1H), 7.98 (s, 1H), 7.60-7.68 (m, 3H), 7.43 (d, 1H), 7.30 (s, 1H), 7.0 (d, 1H), 6.80 (m, 1H), 4.78 (m, 2H), 4.40 (d, 2H), 3.70 (m, 1H), 3.40-3.51 (m, 1H), 3.11 (m, 9H), 2.40 (s, 3H).
  • 9
  • [ 1032759-30-0 ]
  • [ 1332450-87-9 ]
  • [ 1332448-10-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 0.75h;Inert atmosphere; Reflux; Example No. 40Preparation of Compound No. 40[0337] To a solution of 5-(4-bromothiophen-3-yl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.25 mmol) in DME (2 mL) were added water (1 mL) and K2C03 (110 mg, 0.77 mmol) and purged solution with N2. Pd(PPh3)4 (20 mg, 0.017 mmol) and 2-(dimethylamino) pyrimidine-5-boronic acid pinacol ester (140 mg, 0.563 mmol) were added to the reaction mixture, which was refluxed under N2 for 45 min. The reaction mixture was cooled to RT and diluted with EtOAc. Aqueous layer was extracted with EtOAc (3x6 mL) and the combined organic layer dried over sodium sulfate. The solvent was removed under reduced pressure to afford crude material, which was purified by reverse phase HPLC. 1H NMR (TFA salt, CD3OD) d (ppm): 8.0 (m, 3H), 7.80 (dd, 1H), 7.38 (s, 1H), 7.0 (m, 1H), 6.82 (m, 1H), 4.77 (d, 1H), 4.40 (d, 1H), 3.80 (m, 1H), 3.58 (m, 1H), 3.20 (s, 6H), 3.18 (s, 3H), 3.0 (m, 1H), 2.76 (m, 1H), 2.40 (s, 3H).
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 0.75h;Inert atmosphere; Example No. 40: Preparation of Compound No. 40[0328] To a solution of 5-(4-bromothiophen-3-yl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.25 mmol) in DME (2 mL) were added water (1 mL) and K2C03 (110 mg, 0.77 mmol) and purged solution with N2. Pd(PPh3)4 (20 mg, 0.017 mmol) and 2- (dimethylamino) pyrimidine-5-boronic acid pinacol ester (140 mg, 0.563 mmol) were added to the reaction mixture, which was refluxed under N2 for 45 min. The reaction mixture was cooled to RT and diluted with EtOAc. Aqueous layer was extracted with EtOAc (3x6 mL) and the combined organic layer dried over sodium sulfate. The solvent was removed under reduced pressure to afford crude material, which was purified by reverse phase HPLC. 1H NMR (TFA salt, CD3OD) delta (ppm): 8.0 (m, 3H), 7.80 (dd, IH), 7.38 (s, IH), 7.0 (m, IH), 6.82 (m, IH), 4.77 , 7/ (d, in;, <4-.<4-u ^a, iH), 3.80 (m, 1H), 3.58 (m, 1H), 3.20 (s, 6H), 3.18 (s, 3n;, j.u ^m, in;, z. /o(m, 1H), 2.40 (s, 3H).
  • 10
  • [ 1032759-30-0 ]
  • [ 1332450-89-1 ]
  • [ 1332448-14-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 0.75h;Inert atmosphere; Reflux; Example No. 42; Preparation of Compound No. 42[0339] To a de-aerated solution of 5-(3-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), <strong>[1032759-30-0]2-(dimethylamino)pyrimidine-5-boronic acid pinacol ester</strong> (140 mg, 0.561 mmol) and K2C03 (120 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 C for 45 min. The solvent was removed under reduced pressure, residue diluted with water (20 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain crude, which was purified by reverse phase HPLC to yield 5-(3-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)- yl)phenyl)-N,N-dimethylpyrimidin-2-amine. 1H NMR (TFA salt, CD3OD) d (ppm): 8.8 (s, 2H), 7.6-7.77 (m, 3H), 7.4 (d, 1H), 7.3 (s, 1H), 7.1 (d, 1H), 6.97 (d, 1H), 4.77 (d, 1H), 4.4 (d, 1H), 3.8 (m, 1H), 3.5 (m, 1H), 3.3 (s, 6H), 3.1 (m, 4H), 3.0 (m, 1H), 2.4 (s, 3H).
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90.0℃; for 0.75h; Example No. 42: Preparation of Compound No. 42[0330] To a de-aerated solution of 5-(3-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), <strong>[1032759-30-0]2-(dimethylamino)pyrimidine-5-boronic acid pinacol ester</strong> (140 mg, 0.561 mmol) and K2C03 (120 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh )4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 C for 45 min. The solvent was removed under reduced pressure, residue diluted with water (20 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain crude, which was purified by reverse phase HPLC to yield 5-(3-(2,8-dimethyl-3,4-dihydro- lH-pyrido[4,3-b]indol-5(2H)-yl)phenyl)-N,N- dimethylpyrimidin-2-amine. 1H NMR (TFA salt, CD3OD) delta (ppm): 8.8 (s, 2H), 7.6-7.77 (m, 3H), 7.4 (d, 1H), 7.3 (s, 1H), 7.1 (d, 1H), 6.97 (d, 1H), 4.77 (d, 1H), 4.4 (d, 1H), 3.8 (m, 1H), 3.5 (m, 1H), 3.3 (s, 6H), 3.1 (m, 4H), 3.0 (m, 1H), 2.4 (s, 3H).
  • 11
  • [ 1032759-30-0 ]
  • [ 1332450-92-6 ]
  • [ 1332449-33-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90.0℃; for 2h;Inert atmosphere; Example No. 104; Preparation of Compound No. 138[0401] To a de-aerated solution of 5-(5-bromopyridin-2-yl)-2,8-dimethyl-2,3,4,5- tetrahydro-lH-pyrido[4,3-b]indole (100 mg, 0.280 mmol), 2-(dimethylamino)pyrimidine-5- boronic acid pinacol ester (139 mg, 0.557 mmol) and K2CO3 (116 mg, 0.839 mmol) in mixture of DME (4 mL) and water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 C for 2h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated to afford crude material, which was purified by reverse HPLC to yield 5-(6-(2,8-dimethyl-3,4-dihydro- lH-pyrido[4,3-b]indol-5(2H)-yl)pyridin-3-yl)-N,N-dimethylpyrimidin-2-amine as the TFA Salt. 1H NMR (CD3OD, TFA salt) d (ppm): 8.8 (s, IH), 8.71 (s, 2H), 8.24 (d, IH), 7.68 (d, IH), 7.48 (d, IH), 7.37 (s, IH), 7.17 (d, IH), 4.7 (d, IH), 4.3 (d, IH), 3.81 (bs, IH), 3.4-3.6 (m, 3H), 3.3 (s, 6H), 3.18 (s, 3H), 2.42 (s, 3H).
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90.0℃; for 2h; Example No. 104: Preparation of Compound No. 138[0392] To a de-aerated solution of 5-(5-bromopyridin-2-yl)-2,8-dimethyl-2,3,4,5-tetrahydro- lH-pyrido[4,3-b]indole (100 mg, 0.280 mmol), <strong>[1032759-30-0]2-(dimethylamino)pyrimidine-5-boronic acid pinacol ester</strong> (139 mg, 0.557 mmol) and K2C03 (116 mg, 0.839 mmol) in mixture of DME (4 mL) and water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 C for 2h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated to afford crude material, which was purified by reverse HPLC to yield 5-(6-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)- yl)pyridin-3-yl)-N,N-dimethylpyrimidin-2-amine as the TFA Salt. 1H NMR (CD3OD, TFA salt) delta (ppm): 8.8 (s, IH), 8.71 (s, 2H), 8.24 (d, IH), 7.68 (d, IH), 7.48 (d, IH), 7.37 (s, IH), 7.17 (d, IH), 4.7 (d, IH), 4.3 (d, IH), 3.81 (bs, IH), 3.4-3.6 (m, 3H), 3.3 (s, 6H), 3.18 (s, 3H), 2.42 (s, 3H).
  • 12
  • [ 1032759-30-0 ]
  • [ 1382994-99-1 ]
  • [ 1382995-32-5 ]
YieldReaction ConditionsOperation in experiment
50% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100.0℃;Inert atmosphere; Step 2. 1-{5-Chloro-3-[2-(dimethylamino)pyrimidin-5-yl]-2-methoxy-4-methylphenyl}ethanone A biphasic solution of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone (0.10 g, 0.36 mmol) and <strong>[1032759-30-0]N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine</strong> (0.11 g, 0.43 mmol) in 1,4-dioxane (1.2 mL) and 10% sodium carbonate in water (0.57 mL, 0.54 mmol) was bubbled with N2 to degas. After tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.014 mmol) was added, the mixture was bubbled with N2 for 5 min. and heated at 100 C. overnight. The mixture was cooled to r.t. and diluted with ethyl acetate. The layers were separated and the aq. layer was extracted with more ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column, eluting with 0-30% of ethyl acetate in hexane, to give the desired product (60 mg, 50%). LCMS calculated for C16H19ClN3O2 (M+H)+: m/z=320.1. found: 320.1.
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