Copper catalyzed arylation with boronic acids for the synthesis of N 1-aryl purine nucleosides

Tetrahedron Letters

Volumn 46, Issue 34, 2005, Pages 5699-5702

  Strouse, J Jacob ^a   Jeselnik, Marjan ^a   Tapaha, Frederick ^a   Jonsson, Colleen B ^b   Parker, William B ^b   Arterburn, Jeffrey B ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

^b SOUTHERN RESEARCH INSTITUTE   (United States)

Author keywords

Copper; Coupling; Heteroatom; Nucleoside

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER; GUANOSINE DERIVATIVE; INOSINE; PURINE DERIVATIVE; PURINE NUCLEOSIDE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 22544485971     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.083     Document Type: Article

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28. Typical procedure: To an oven dried Schlenk tube were added the protected nucleoside (0.2 mmol), the boronic acid (0.4 mmol), anhydrous copper(II) acetate (0.04 mmol), pyridine-N-oxide (0.4 mmol), ground 4 Å molecular sieves (∼20 mg), and a stir bar. The tube was sealed with a septum then evacuated and flushed with oxygen. Dry pyridine (0.4 mmol) and dichloromethane (2 mL, dried over molecular sieves) were then added and the solution was stirred vigorously at room temperature for 24 h. The reaction was then quenched with ammonium hydroxide in methanol (∼0.05 mL in 1 mL, respectively) followed by dilution with hexanes (to 50 mL) and washed with one 25 mL portion each of water, saturated ammonium chloride, 1 M sodium hydroxide, and saturated sodium chloride. The organics were dried over sodium sulfate and concentrated in vacuo. Compounds were purified by medium pressure flash chromatography (Isco CombiFlash) with methanol/dichloromethane.
29. 3: C, 58.62; H, 8.43; N, 7.81.
30. 3: C, 57.42; H, 8.40; N, 9.57.