Ethylenediamine → HCID 78132840, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-ethyl-N2-(1-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethyl)pyrimidine-2,4-diamine (103.9 mg, 0.20 mmol) in anhydrous DMF (4.7 mL) was added ethylenediamine (0.10 mL, 1.60 mmol) followed by tetrabutylammonium fluoride (1M in THF, 0.60 mL, 0.60 mmol), and the reaction mixture was stirred at 80° C. under N2 for 20 h. The reaction mixture was poured into EtOAc, and the organic layer was washed with 10% aq. NaOH solution, water and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 chromatography to afford 50.4 mg (64.7%) of racemic N2-(1-(5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-ethylpyrimidine-2,4-diamine. Chiral SFC chromatography of racemic N2-(1-(5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-ethylpyrimidine-2,4-diamine (50.4 mg, 0.13 mmol) afforded the corresponding two enantiomers:

Provenance & Evidence