反应 #1509654

反应方程式

6-chloro-2-iodo-9-isopropyl-9H-purine

benzo[b]thiophen-3-ylboronic acid

toluene

sodium carbonate

→

title compound

2-(benzo[b]thiophen-3-yl)-6-chloro-9-isopropyl-9H-purine

溶剂

ethanol

Water

反应条件

后处理

1. 1
   其他The flask was sealed
2. 2
   萃取was extracted with ethyl acetate
3. 3
   干燥dried over sodium sulfate
4. 4
   浓缩concentrated
5. 5
   其他The residue was purified by column chromatography on silica gel
6. 6
   洗涤eluting with 20 to 50% EtOAc in hexane

实验过程

A round-bottom flask was charged with 6-chloro-2-iodo-9-isopropyl-9H-purine (prepared in Example 15c, 3.31 g, 0.0103 mol), benzo[b]thiophen-3-ylboronic acid (2.74 g, 0.0154 mol), and tetrakis(triphenylphosphine)palladium(0) (1.19 g, 0.0103 mol). To this mixture was added toluene (80 ml), ethanol (25 ml) and aqueous sodium carbonate solution (2M, 21 ml). The flask was sealed and the reaction mixture was stirred at 90° C. for 1 h. Water was added to the cooled mixture, which was extracted with ethyl acetate. The organic fractions were combined, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel, eluting with 20 to 50% EtOAc in hexane to afford the title compound as a solid, which was recrystallized from 1:1 methanol/water. 1H NMR (400 MHz, DMSO-d6): δ=9.15 (d, 1H), 8.85 (s, 2H), 8.17 (d, 1H), 7.62 (t, 1H), 7.53 (t, 1H), 5.06 (m, 1H), 1.71 (d, 6H); MS m/z 329.0 (M+1).

来源