反应 #1509658

反应方程式

4-(2-(2-chloro-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol

thianaphthene-3-boronic acid

potassium carbonate

→

title compound

4-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol

溶剂

DMA

water

water

Ethyl acetate

反应条件

后处理

1. 1
   过滤the mixture was filtered through Celite (125 g) at 50° C.
2. 2
   洗涤rinsing with ethyl acetate (1.0 L)
3. 3
   其他The layers were separated
4. 4
   萃取the aqueous layer was extracted at 50° C. with additional ethyl acetate (7.5 L)
5. 5
   洗涤The combined organic layers were washed with water (3×2.5 L)
6. 6
   workup.DISTILLATIONdistilled
7. 7
   其他to remove about 2.5 L of solvent
8. 8
   workup.ADDITIONTetrahydrofuran (2.5 L) and silica bond thio silica gel (200 g) were added
9. 9
   workup.STIRRINGThe mixture was stirred at 70° C. for 16 hr
10. 10
    过滤was filtered
11. 11
    洗涤washing the pad with ethyl acetate (1.0 L)
12. 12
    浓缩The combined filtrates were concentrated at atmospheric pressure to a volume of about 5 L
13. 13
    温度to cool
14. 14
    其他The resulting solid was collected
15. 15
    洗涤washed with ethyl acetate (2×1.0 L)

实验过程

A mixture of 4-(2-(2-chloro-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol (950 g), thianaphthene-3-boronic acid (561 g), dichlorobis(triphenylphosphine)palladium(II) (10.1 g), potassium carbonate (791 g), water (3.25 L), and DMA (3.25 L) was stirred under a nitrogen atmosphere for 10 min. The stirred mixture was then heated at 70° C. for 14 h. Ethyl acetate (6.5 L) and water (3.25 L) were added, and the mixture was filtered through Celite (125 g) at 50° C., rinsing with ethyl acetate (1.0 L). The layers were separated, and the aqueous layer was extracted at 50° C. with additional ethyl acetate (7.5 L). The combined organic layers were washed with water (3×2.5 L), then distilled to remove about 2.5 L of solvent. Tetrahydrofuran (2.5 L) and silica bond thio silica gel (200 g) were added. The mixture was stirred at 70° C. for 16 hr, then was filtered, washing the pad with ethyl acetate (1.0 L). The combined filtrates were concentrated at atmospheric pressure to a volume of about 5 L, then the mixture was allowed to cool. The resulting solid was collected and washed with ethyl acetate (2×1.0 L) to provide the title compound.

来源