Diisopropylethylamine → HCID 136247181, compound

Participants

Reaction Conditions

Reaction Steps

A microwave reaction vial was charged with 2-chloro-7-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Intermediate A) (25 mg, 0.13 mmol), 4-(4-fluorophenyl)piperidine hydrochloride (35.2 mg, 0.16 mmol), and N,N-diisopropylethylamine (52.8 mg, 0.41 mmol) in ethanol (1.5 mL). The vial was sealed and then heated in the microwave at 140° C. for 15 min. At this time, the resulting mixture was concentrated in vacuo. Flash chromatography (20/1 methylene chloride/methanol) afforded 2-[4-(4-fluoro-phenyl)-piperidin-1-yl]-7-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (44.4 mg, 36%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.5-1.7 (m, 2H) 1.8 (d, J=11.55 Hz, 2H) 2.8 (br. s., 1H) 2.9 (t, J=12.05 Hz, 2H) 3.5 (s, 3H) 4.5 (d, J=13.05 Hz, 2H) 6.2 (d, J=3.51 Hz, 1H) 6.7 (d, J=3.26 Hz, 1H) 7.1 (t, J=8.78 Hz, 2H) 7.3 (dd, J=8.53, 5.52 Hz, 2H) 10.7 (s, 1H). LC-MS calcd. for C18H20FN4O [(M+H)+] 327, obsd. 327.0.

Provenance & Evidence