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ChemicalBook CAS DataBase List 9-benzyl-2,6-dichloro-9H-purine
79064-26-9

9-benzyl-2,6-dichloro-9H-purine synthesis

11synthesis methods
Benzyl bromide

100-39-0

2,6-Dichloropurine

5451-40-1

9-benzyl-2,6-dichloro-9H-purine

79064-26-9

27.1 Preparation of 9-benzyl-2,6-dichloro-9H-purine Potassium carbonate (2.07 g, 15 mmol) was added to a solution of 2,6-dichloro-9H-purine (945 mg, 5.0 mmol) in dimethylformamide (20 mL) and the mixture was stirred at room temperature for 30 minutes. Benzyl bromide (1.2 mL, 10 mmol) was then added and the mixture was stirred overnight. Upon completion of the reaction, water was added and the resulting mixture was extracted with ethyl acetate. The organic extracts were combined, washed sequentially with water and brine, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by rapid chromatography on silica gel column (Presearch Combiflash Rf) with ethyl acetate/hexane (0% to 80% gradient) as eluent gave 9-benzyl-2,6-dichloro-9H-purine as a white solid. The compound was characterized by the following data: 1H NMR (400 MHz, CDCl3) δ 8.10 (1H, s), 7.40 (5H, m), 5.40 (2H, s) ppm. 27.2 Preparation of 9-benzyl-2-chloro-6-trimethylmethylstannyl-9H-purine

-

Yield:79064-26-9 96%

Reaction Conditions:

with di-isopropyl azodicarboxylate;triphenylphosphine in tetrahydrofuran at 70; for 12 h;Mitsunobu coupling;

References:

Lu, Weibing;Sengupta, Sujata;Petersen, Jeffrey L.;Akhmedov, Novruz G.;Shi, Xiaodong [Journal of Organic Chemistry,2007,vol. 72,# 13,p. 5012 - 5015]

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