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With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere;
To a reaction flask were added compound 27-c (36 mg, 0.106 mmol), compound 38-b (prepared according to the method disclosed in: WO 2011/079230 A2) (20 mg, 0.106 mmol), PdC12(dppf) (4 mg, 0.005 mmol), 2 N sodium carbonate aqueous solution (0.16 mE, 0.32 mmol, 3.0 equiv.) and 1 ,4-dioxane (1 mE). The mixture was stirred under nitrogen atmosphere at 80 C. overnight. The reaction mixture was concentrated under reduced pressure, and then partitioned between water (15 mE) and dichioromethane (20 mE). The organic phase was separated out, dried over anhydrous sodium sulfate, and concentrated under reduced pressure, to obtain compound 38-a (40 mg). EC-MS (ESI): mlz=354.7 (M+H).
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chlorofuro[3,2-d]pyrimidin-4-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
85%
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃; for 5.0h;
[0111] A mixture of 2,4-dichlorofuro[3,2-d]pyrimidine (150 mg, 0.79 mmol), 4-(lH- pyrazol-4-yl)aniline (126.3 mg, 0.79 mmol), and diisopropylethylamine (0.28 mL, 1.59 mmol) in DMF (1.59 mL) was heated at 100 C for 5 h. TLC showed the reaction was complete. The mixture was then diluted with water. The resulted yellow precipitate was filtered and washed with water and dried in vacuo to provide 210 mg (85%) title compound which was used directly for next step reaction without further purification.
2-chloro-4-(((1r,4r)-4-morpholinocyclohexyl)oxy)furo[3,2-d]pyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
60%
A mixture of(lr,4r)-4-morpholinocyclohexan-1-ol (0.53 g, 2.9 mmol, 1.1 eq) in 5.0 mL of THF was prepared and 60% NaH (0.56 g, 14 mmol, 5.3 eq) was added. The reaction mixture was stirred at room temperature for 30 mm and 2,4-dichlorofuro[3,2-djpyrimidine (0.50 g, 2.6 mmol, 1.0 eq) was added and the resulting mixture was heated at 60 C for 3 hr. The reaction was cooled to room temperature and quenched with saturated aqueous ammonium chloride. The quenched mixture was rotary evaporated and purified on normal phase Combi-Flash using a 40 g column and eluting with a gradient of 0-20% MeOH/CH2C12 in 10 mm. The product containing fractions were combined and rotary evaporated to give 2-chloro-4-(((lr,4r)-4- morpholinocyclohexyl)oxy)furo[3,2-djpyrimidine (0.59 g, 1.7 mmol, 60% yield) as a white solid. LC-MS:M+H=338.0
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