4,6-dichloro-N-methyl-N-(prop-2-yn-1-yl)pyrimidine-5-carboxamide → 4-Chloro-1,2-dihydro-2-methyl-3H-pyrrolo[3,4-c]pyridin-3-one

Participants

Reaction Steps

A solution of 4,6-dichloro-N-methyl-N-(prop-2-yn-1-yl)pyrimidine-5-carboxamide (Compound 310F, 7.6 g, 31 mmol) in Nitrobenzene (76 mL) was evacuated and purged with argon (3×). The reaction mixture was irradiated in the microwave for 1.5 minutes at 250° C. The reaction mixture was filtered through a pad of celite. The nitrobenzene solution was passed through a silica gel plug and washed with DCM to remove the nitrobenzene. The silica was then washed with DCM/MeOH solution (90:10). The filtrated was concentrated under reduced pressure to yield a red solid. The crude material was purified by silica gel chromatography on a combi-flash Rf system using DCM/MeOH (100:0→95:5) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield an orange solid (3.1598 g, 56%). 1H NMR (DMSO-d6, 400 MHz): δ=8.53 (d, J=5.05 Hz, 1H), 7.70 (d, J=5.05 Hz, 1H), 4.53 (s, 2H), 3.05 (s, 3H). MS (ES+): m/z 183.02 [MH+] (TOF, polar).

Provenance & Evidence