N'-(2-amino-7-(2-((2-((2,4-difluorophenyl)(methyl)amino)ethyl)(methyl)amino)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide → N1-(2-(5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)-N2-(2,4-difluorophenyl)-N1,N2-dimethylethane-1,2-diamine

Participants

Reaction Conditions

Reaction Steps

The title C compound, N′-(2-amino-7-(2-((2-((2,4-difluorophenyl)(methyl)amino)ethyl)-(methyl)amino)ethyl) -7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide (crude from the previous step) (0.50 mmol) is dissolved in 2 mL of HMDS and 2 mL of BSA. The mixture is heated at 120° C. overnight, then cooled down to RT and the solvent removed in vacuo. The residue is dissolved in a mixture of DCM (2 mL) and 6N aqueous HCl (2 mL), and stirred at RT for 1 h. The pH value is adjusted to 12 using 1M aqueous NaOH. The organic phase is separated and the aqueous phase is extracted with additional DCM. The combined organic phase is dried over anhydrous Na2SO4, filtered and evaporated. The residue is purified by flash chromatography to obtain N1-(2-(5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)-N2-(2,4-difluorophenyl)-N1,N2-dimethylethane-1,2-diamine: LC/MS (M+1=467). 1H NMR (DMSO-d6) δ 2.22 (s, 3H), 2.42-2.49 (m, 2H), 2.65 (s, 3H), 2.72 (t, 2H, J=6.37 Hz), 3.01 (t, 2H, J=6.81 Hz), 4.16 (t, 2H, J=6.37 Hz), 6.57 (d, 1H, J=3.42 Hz), 6.70 (dd, 1H, J=3.39 Hz and 1.78 Hz), 6.75-6.90 (m, 2H), 7.01-7.16 (m, 2H), 7.18 (dd, 1H, J=3.39 Hz and 0.81 Hz), 7.47 (s, 2H), 7.99 (dd, 1H, J=1.73 Hz and 0.81 Hz).

Provenance & Evidence