반응 #74070

반응 방정식

water

2-bromo-N,N-dimethylethanamine

ethyl 8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

cesium carbonate

→

ethyl 1-[2-(dimethylamino)ethyl]-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

용매

dimethylformamide

반응 조건

후처리

1. 1
   추출extracted with EtOAc
2. 2
   세척The organic layer washed with brine
3. 3
   건조dried over Na2SO4
4. 4
   농축concentrated
5. 5
   기타The crude was purified by silica gel chromatography
6. 6
   세척eluting with EtOAc/Ethanol 85/15

실험 절차

To a solution of ethyl 8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (150 mg, 0.52 mmol) in dry dimethylformamide (4 ml) was added cesium carbonate (339 mg 1.04 mmol) followed by 2-bromo-N,N-dimethylethanamine (135 mg 0.88 mmol). The heterogeneous mixture was stirred at room temperature for 24 hours. The mixture was treated with water and extracted with EtOAc. The organic layer washed with brine, dried over Na2SO4 and concentrated. The crude was purified by silica gel chromatography eluting with EtOAc/Ethanol 85/15 to give ethyl 1-[2-(dimethylamino)ethyl]-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate as the major isomer (60 mg 32%) 1H NMR (401 MHz, DMSO-d6) δ 9.51 (s, 1H), 8.16 (d, J=8.67 Hz, 1H), 7.83 (d, J=8.79 Hz, 1H), 5.29 (t, J=6.59 Hz, 1H), 4.32-4.49 (m, 2H), 2.94 (br. s., 2H), 2.71 (s, 3H), 2.24 (br. s., 6H), 1.41 (t, J=7.08 Hz, 3H); and

출처