1,4-Dioxane → HCID 67116616, compound

Participants

Reaction Steps

To a solution of 2-bromopyridin-3-yl)(5-(4,6-dimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone (Example 234) (150 mg, 0.37 mmol), 1H-1,2,3 triazole (43 μL, 0.75 mmol), CsCO3 (247 mg, 0.75 mmol), in H2O (2 μL) and 1,4 dioxane (2 mL) was added (R,R)-(−)-N,N′-dimethyl-1,2-cyclohexyldiamine (12 μL, 0.75 mmol) and CuI (3.5 mg, 0.86 mmol). The reaction mixture was irradiated in a microwave reactor at 160° C. for 2 h. The resulting solution was filtered through Celite®, washed with DCM, and concentrated. Purification (FCC)(MeOH(NH3)/DCM) gave the title compound (8 mg, 6%). MS (ESI): mass calculated for C20H22N8O, 390.19; m/z found 391.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.65 (dd, J=4.8, 1.8, 1H), 7.83 (dt, J=13.3, 6.6, 2H), 7.43 (dt, J=7.6, 4.5, 1H), 6.38-6.23 (m, 2H), 4.02-3.28 (m, 6H), 3.10-3.06 (m, 4H), 2.42-2.22 (m, 6H).

Provenance & Evidence