Iodoethane → HCID 67385558, compound

Participants

Reaction Steps

Bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (54 mg) was dissolved in dimethylformamide (5 ml), and sodium hydride (60% mineral oil dispersion, 5 mg) was added under ice cooling, followed by stirring at room temperature for 30 minutes. After dropwise addition of ethyl iodide (9 μl), the reaction mixture was further stirred for 10 hours, and subsequently diluted with water (20 ml), followed by extraction with ethyl acetate (10 ml×2). The combined organic layers were washed with brine, and dried with sodium sulfate. After filtering off the drying agent, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/0 to 10/1), to obtain [5-(7-ethyl-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-bis-(4-methoxy-benzyl)-amine as a colorless solid (49 mg, 86%). The above colorless solid was dissolved in trifluoroacetic acid (2 ml), and concentrated sulfuric acid (1 drop) was added, followed by stirring at 100° C. for 1 hour. The solvent was concentrated under reduced pressure, and the resulting residue was diluted with water (2 ml), to filter the resulting precipitate, followed by washing with water. The crude product was purified by amino silica gel column chromatography (dichloromethane), to obtain a colorless powder (18 mg, 64%).

Provenance & Evidence