3,4-dihydro-2H-pyran → 6-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

Participants

Reaction Conditions

Reaction Steps

A solution of 6-bromo-9H-purine (2.0 g, 10 mmol) and p-toluenesulfonic acid monohydrate (190 mg, 1.0 mmol) in chloroform (45 mL) at 0° C. was treated with dihydropyran (1.4 mL, 15 mmol) and stirred at 20° C. for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with saturated sodium bicarbonate, water and brine, dried with sodium sulfate, filtered, and concentrated to give a crude residue. Purification by flash column chromatography using ethyl acetate in hexanes (0%-70%) gave the desired product (2.7 g, 94%). LCMS for C10H12BrN4O (M+H)+: m/z=283.0, 285.0; Found: 283.0, 285.0.

Provenance & Evidence