反应详情

温度

80 °C

Diisopropylethylamine (0.35 mL, 2.01 mmol) was added at room temperature to a suspension of 4-(2-amino-4-chloro-phenoxy)-cyclohexanol (127 mg, 0.525 mmol), pyrazolo[1,5-c]pyrimidine-3-carboxylic acid (85 mg, 0.521 mmol) and HBTU (0.21 g, 0.55 mmol) in anhydrous acetonitrile (15 mL) and the resulting solution was heated at 80° C. overnight. The resulting mixture was partitioned between ethyl acetate and an aqueous solution of sodium bicarbonate (5%). The aqueous layer was extracted 3 times with ethyl acetate and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The brown oily residue was purified on a silica gel plug and by flash chromatography (DCM/MeOH/NH4OH) to give a pale yellow solid which was washed with dichloromethane and methanol to give 75 mg (38% yield) of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-chloro-2-(4-hydroxy-cyclohexyloxy)-phenyl]-amide as a white powder. MS=387 [M+H]+.

1. customThe resulting mixture was partitioned between ethyl acetate
2. extractionThe aqueous layer was extracted 3 times with ethyl acetate
3. washthe combined organic extracts were washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customThe brown oily residue was purified on a silica gel plug and by flash chromatography (DCM/MeOH/NH4OH)
8. customto give a pale yellow solid which
9. washwas washed with dichloromethane and methanol