Cesium carbonate → tert-butyl rel-[(3S,4S)-3-({6-cyano-5-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl rel-{(3S,4S)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate (Enantiomer 1 from previous step) (50 mg, 0.11 mmol), 4-methoxy-6-methylpyridin-2-amine (16 mg, 0.11 mmol), Pd2(dba)3 (10 mg, 0.011 mmol), cesium carbonate (91 mg, 0.28 mmol), and Xanthpos (13 mg, 0.022 mmol) was purged with argon for 5 minutes. 1,4-Dioxane (1.0 ml) was added, and the reaction mixture was purged with argon for 5 minutes, and then heated to 90° C. for 2 hours. The reaction mixture was cooled to room temperature, filtered through CELITE, and concentrated under reduced pressure to afford tert-butyl rel-[(3S,4S)-3-({6-cyano-5-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]carbamate, which was used directly in the next step without purification. MS ESI calc'd. for C23H31N6O5S [M+H]+ 503. found 503.

Provenance & Evidence