反应详情

温度

95 °C

Copper(II) acetate monohydrate (83 mg, 041 mmol) was added to a mixture of 2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (0.1 g, 0.41 mmol), cyclopropylboronic acid (35 mg, 0.41 mmol) and DMAP (75 mg, 0.617 mmol) in toluene (1 mL). The mixture was stirred at 95° C. for 16 hours. The mixture was stirred at 95° C. for 24 hours more. The reaction was allowed to room temperature and was poured into a 1N solution of HCl and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo. The desired product was triturated with diethyl ether to yield 5-cyclopropyl-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (19 mg, 16% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 0.68-0.79 (m, 2H), 0.89-1.00 (m, 2H), 2.74-2.82 (m, 1H), 3.74-3.82 (m, 2H), 4.30-4.37 (m, 2H), 5.08 (s, 2H), 6.93 (s, 1H), 6.94-6.97 (m, 1H), 6.98-7.02 (m, 2H), 7.26-7.31 (m, 2H).

1. stirringThe mixture was stirred at 95° C. for 24 hours more
2. customwas allowed to room temperature
3. extractionextracted with AcOEt
4. customThe organic layer was separated
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50)
9. customThe desired fractions were collected
10. customthe solvents evaporated in vacuo
11. customThe desired product was triturated with diethyl ether