1-(4-Pyridyl)piperazine → HCID 136247062, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-7-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Intermediate A) (50.1 mg, 273 μmol) in ethanol (730 μL) was treated with 1-(pyridin-4-yl)piperazine (51.8 mg, 317 μmol) and N,N-diisopropylethylamine (46.7 mg, 63.10 μL, 361 μmol). The reaction stirred at 100° C. overnight. At this time, the reaction was diluted with methanol and methylene chloride and concentrated in vacuo onto Celite®. Flash chromatography (4 g silica gel column, 10% methanol/methylene chloride) afforded 7-methyl-2-(4-pyridin-4-yl-piperazin-1-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (43 mg, 50.8%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.48 (d, J=4.33 Hz, 4H) 3.57 (s, 3H) 3.69 (d, J=6.03 Hz, 4H) 6.25 (d, J=3.39 Hz, 1H) 6.78 (d, J=3.20 Hz, 1H) 6.91 (d, J=6.97 Hz, 2H) 8.19 (d, J=6.40 Hz, 2H) 10.90 (s, 1H). LC-MS calcd. for C16H19N6O [(M+H)+] 311, obsd. 311.1.

Provenance & Evidence