Water → 2-(furan-2-yl)-7-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (13 mg, 0.32 mmol) in anhydrous DMF (2 mL) at 0° C. is added slowly a solution of the title B compound, 2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine (60 mg, 0.25 mmol) in 2 mL of anhydrous DMF. After stirring at 0° C. under N2 for 15 min, 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine (0.275 mmol) is added at 0° C. The mixture is warmed to RT and stirred overnight. The reaction mixture is then poured into water and extracted with DCM (3×). The organic layer is dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product is purified by flash chromatography using DCM/MeOH/NH4OH (98/2/0 2) as eluent to give 2-(furan-2-yl)-7-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine: LC/MS (M+1=459.2). 1H NMR (DMSO-d6, 400 MHz) δ 2.56 (m, 4H), 2.67 (t, 2H, J=6.0 Hz), 2.94 (m, 4H), 3.76 (s, 3H), 4.28 (t, 2H, J=6.0 Hz), 6.60 (d, 1H, J=3.2 Hz), 6.71 (m, 1H), 6.85 (m, 2H), 6.92 (m, 2H), 7.18 (m, 2H), 7.49 (brs, NH2), 7.91 (d, 1H, J=1.6 Hz).

Provenance & Evidence