Reaction #1509653

Reaction equation

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

thianaphthene-3-boronic acid

Cs2CO3

1,3-bis(2,4,6-trimethylphenyl) imidazolium chloride

→

title compound

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

Conditions

Workup

1. 1
   OtherThe flask was evacuated
2. 2
   workup.ADDITIONwas added
3. 3
   OtherThe flask was sealed
4. 4
   ConcentrationThe reaction mixture was concentrated
5. 5
   Otherpurified directly by column chromatography on silica gel
6. 6
   Washeluting with hexane/EtOAc (20:1 to 1:4)

Procedure

A flame-dried schlenk flask was charged with 4-(2-(2-chloro-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol (0.62 mmol), thianaphthene-3-boronic acid (0.94 mmol), pd2(dba)3 (0.062 mmol), Cs2CO3 (1.25 mmol) and 1,3-bis(2,4,6-trimethylphenyl) imidazolium chloride (0.125 mmol). The flask was evacuated and backfilled with N2 and anhydrous 1,4-dioxane (2 mL) was added. The flask was sealed and the reaction mixture was stirred at 80° C. for 24 hours. The reaction mixture was concentrated and purified directly by column chromatography on silica gel, eluting with hexane/EtOAc (20:1 to 1:4) to afford the title compound as a yellowish solid.

Source