反应详情

温度

60 °C

A solution of 1-benzyl-5′-oxo-2′-(4-phenoxyphenyl)-5′,6′-dihydro-4′H-spiro[piperidine-4,7′-pyrazolo[1,5-a]pyrimidine]-3′-carboxamide (180 mg, 0.36 mmol) in BH3/THF (IN, 20 mL) was heated to reflux for 3 hr. The reaction was quenched with MeOH (20 mL) and con. HCl (2 mL). The mixture was stirred at 60° C. for 1 hr, then was basified with NaHCO3 and extracted with EA (20 mL×3). The combined organic layers were dried over Na2SO4, concentrated and purified by chromatography column on silica gel eluting with 5% of MeOH in DCM to give the product (120 mg, 67.6%) as a yellow solid. 1H NMR (400 MHz, CD3OD-d4) δ 7.39-7.22 (m, 9H), 7.09-7.04 (m, 1H), 6.99-6.94 (m, 4H), 3.86 (s, 2H), 3.35 (t, J=5.6 Hz, 2H), 3.19-3.11 (m, 2H), 2.80-2.66 (m, 2H), 2.50-2.40 (m, 2H), 2.10 (t, J=5.6 Hz, 2H), 1.87-1.78 (m, 2H). MS (ESI, m/e) [M+1]+ 493.9.

1. temperatureto reflux for 3 hr
2. customThe reaction was quenched with MeOH (20 mL)
3. extractionextracted with EA (20 mL×3)
4. dry with materialThe combined organic layers were dried over Na2SO4
5. concentrationconcentrated
6. custompurified by chromatography column on silica gel eluting with 5% of MeOH in DCM