反应 #1702148

反应方程式

HCl

3-{3-[(2-{[3-(2-bromoethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]propyl}phenol

sodium hydroxide

→

desired product

收率 11.0%

21-Chloro-10-oxa-2,19,23,24-tetraazatetracyclo[18.3.1.1(3,7).1(11,15)]hexacosa-1(24),3(26),4,6,11(25),12,14,20,22-nonaene

收率 11.0%

溶剂

tetrahydrofuran

water

反应条件

后处理

1. 1
   萃取The aqueous layer was extracted with EtOAc three times
2. 2
   干燥The combined organic layers were dried over Na2SO4
3. 3
   过滤filtered
4. 4
   浓缩concentrated
5. 5
   其他to give the crude, which
6. 6
   其他was purified by silica gel column chromatography

实验过程

To a solution of 3-{3-[(2-{[3-(2-bromoethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]propyl}phenol (50.0 mg, 0.108 mmol) in tetrahydrofuran (1.0 mL) was added a solution of sodium hydroxide in water (1.0 mL, 1.0 M). The resultant solution was stirred at rt for 60 hours until the reaction was complete. The reaction mixture was neutralized with HCl (3 M aqueous solution) to pH=7. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product as a white powder (4.5 mg, 11%). LCMS for C21H22ClN4O (M+H)+: m/z=381.0. 1H NMR (400 MHz, CD3OD): δ 7.98 (s, 1H), 7.92 (s, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.40 (m, 1H), 7.06 (m, 1H), 6.97 (s, 1H), 6.70 (d, J=2.4 Hz, 1H), 6.62 (m, 2H), 3.60 (m, 4H), 3.20 (m, 2H), 2.68 (t, J=7.6 Hz, 2H), 2.02 (t, J=7.6 Hz, 2H).

来源