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ChemicalBook CAS DataBase List N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine
2312-73-4

N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine synthesis

6synthesis methods
Dissolve alcohol in PrOH (14 ml). Add TEA (0.95 ml, 6.9 mmol) and 6-chloro-9-(tetrahydropyran-2-yl)purine (1.64 g) to the reaction mixture. Heat the reaction mixture at 45 °C for 6 hours. Cool the reaction mixture. Filter the mixture. Evaporate the filtrate partly. Purify the filtrate by CC (60.3 g of silica gel, mobile phase CHCl3-Me2CO 4:1, flow rate 7.5 ml/min). The product is a light yellow viscous substance that starts to crystallize after two weeks of drying over P2O5 in a vacuum desiccator.
Preparation of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine Figure Preparation of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine
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Yield:2312-73-4 66%

Reaction Conditions:

with triethylamine in isopropyl alcohol at 40; for 8 h;

Steps:

2 6-Benzylamino-9-( tetrahydropyran-2-yl)-9H-purine
6-Chloro-9-(tetrahydropyran-2-yl)-9H-purine (Ex 1.) (2.52 g, 10.6 mmol) was dissolved in 2- propanol (13.5 ml). Benzylamine (1.4 ml, 12.8 mmol) and triethylamine (1.5 ml, 10.5 mmol) were added. The solution was stirred and heated at 40 °C for 8 h. The mixture was evaporated to dryness, dissolved in 20 ml of ethyl acetate and extracted with 15 ml of water twice. Ethyl acetate layer was dried with Na2S04 and evaporated. The crude product crystallizes after drying in desiccator with P205 to give (2.14 g, 66 %). white crystals, m. p. : 124-127 °C. MS ESI+ (CV 10) m/z (rel. %): 310 [M+H]+ (100); (CV 40) m/z (rel. %): 226 [Ci2H„N5+H]+ (100), 310 [M+H]+

References:

USTAV EXPERIMENTALNI BOTANIKY AV CR, V.V.I.;ZAHAJSKA, Lenka;NISLER, Jaroslav;KADLECOVA, Alena;ZATLOUKAL, Marek;GRUZ, Jiri;VOLLER, Jiri;DOLEZAL, Karel;STRNAD, Miroslav WO2016/95880, 2016, A1 Location in patent:Page/Page column 19

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