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6-ethynyl-3-[4-((1S,3R,5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-yloxy)phenyl]-3H-thieno[3,2-d]pyrimidin-4-one[ No CAS ]
6-furo[3,2-b]pyridin-2-yl-3-[4-((1S,3R,5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-yloxy)phenyl]-3H-thieno[3,2-d]pyrimidin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In toluene; at 90℃; for 5h;
6-Ethynyl-3-[4-((l S,3R,5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-yloxy)phenyl]-3H-thieno[3,2- d]pyrimidin-4-one (39.2 mg), bis(triphenylphosphine)palladium chloride (3.5 mg) and copper iodide (0.95 mg) were added to a solution of 2-iodo-3-pyridinol (22.1 mg) and triethylamine (0.272 mL) in toluene (1.36 mL). The reaction mixture was heated at 900C for 5 hours. The solvent was then removed in vacuo, the residue was taken up in ethyl acetate and water, and the organic phase was acidified with 2N hydrochloric acid. The organic phase was then washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC. The product with the molecular weight of 484.58 (C27H24N4O3S) was obtained in this way; MS (ESI): 485 (M+H+).
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 70℃; for 16h;Under nitrogen;
Intermediate 11 Ethyl ?-^-furotS^-blpyridin^-yOpheny^-Z-I^frans-?methylcyclohexylJcarbonylKI- methylethyl)amino]-3-furancarboxylateTo Intermediate 10 (78 mg) was added <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (40.8 mg), bis(triphenylphosphine)palladium dichloride (13 mg), copper (I) iodide (3.5 mg) and triethylamine (1.2 mL). The reaction was stirred at 7O0C, under nitrogen, for 16 h. The reaction was cooled, partitioned between saturated sodium bicarbonate solution and DCM1, passed through a hydrophobic and then concentrated. The crude product was dissolved in DCM, filtered and purified by ISCO companion silica chromatography eluting with a gradient of ethyl acetate in cyclohexane (0% to 100%) to give the title compound. MS calcd for (C3IH34N2O5 + H)+: 515 MS found (electrospray): (M+H)+ = 515
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 70℃; for 17h;
Intermediate 33Ethyl 5-(4-furo[3,2-b]pyridin-2-ylphenyl)-2-[[(fra?s-4- methylcyclohexyl)carbonyl](tetrahydro-3-furanyl)amino]-3-furancarboxylateA mixture of Intermediate 32 (228 mg), <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (112 mg), copper(l) iodide (10 mg), dichlorobis(triphenylphosphine)palladiurr) (II) (36 mg) and triethylamine (3.5 ml_) were stirred and heated in a Reacti-vial at 700C for 17 h. The reaction was cooled, partitioned between saturated sodium bicarbonate solution and DCM, separated using a hydrophobic frit and the organics were evaporated in vacuo. The crude material was purified by ISCO Companion silica chromatography, eluting with a gradient 0-100% EtOAc in cyclohexane to give the title compound. MS calcd for (C32H34N2O6 + H)+: 543 MS found (electrospray): (M+H)+ = 543
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 70℃;
Intermediate 37Ethyl 5-(4-furo[3,2-b]pyridin-2-ylphenyl)-2-[(frans-4-methylcyclohexyl)carbonyl][2- (methyloxy)ethyl]amino}-3-furancarboxylateA mixture of Intermediate 36 (220 mg), 2-?odo-3-hydroxypy?d?ne (1 12 mg), copper(l) iodide (10 mg), d?chlorob?s(t?phenylphosphine)pallad?um (II) (36 mg) and triethylamine (3 5 ml_) were heated in a Reacti-vial at 7O0C overnight. The reaction was cooled to room temperature, partitioned between saturated sodium bicarbonate solution and DCM, separated using a hydrophobic frit and the organics were evaporated in vacuo The crude material was purified by ISCO Companion silica chromatography, eluting with a gradient 0- 100% EtOAc in cyclohexane to give the title compound. MS calcd for (C31H34N2O6 + H)+- 531 MS found (electrospray)- (M+H)+ = 531
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