Ethylamine hydrochloride → HCID 86762625, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial charged with 1-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethanone (1.50 g, 5.15 mmol), ethylamine hydrochloride (3.36 g, 41.2 mol), sodium cyanoborohydride (420.5 mg, 6.69 mmol), and anhydrous EtOH (40 mL) was stirred under microwave irradiation (300 Watts) at 130° C. for 2 min. The solid was filtered and rinsed well with EtOH. Volatile solvent from the filtrate was removed under reduced pressure. The resultant crude was redissolved in EtOAc and washed with 10% aqueous NaOH solution (2×), water, and brine. The organic phase was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude was triturated in DCM, and the insoluble solid was filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure and dried on high-vac to afford N-ethyl-1-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethanamine as an oil. 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 7.50 (d, J=3.2 Hz, 1H), 6.65 (d, J=3.2 Hz, 1H), 5.50 (s, 2H), 4.09 (q, J=6.7 Hz, 1H), 3.46 (t, J=8.1 Hz, 2H), 2.57 (dd, J=11.2, 7.2 Hz, 1H), 2.46 (dd, J=11.2, 7.0 Hz, 1H), 2.08 (br s, 1H), 1.46 (d, J=6.7 Hz, 3H), 1.08 (t, J=7.1 Hz, 3H), 0.88 (t, J=8.1 Hz, 2H), −0.07 (d, J=0.9 Hz, 9H)); MS (ESI) m/z: 321.4 [M+1]+.

Provenance & Evidence