Sodium Bicarbonate → HCID 58504530, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-N-methyl-6-[(2S)-2-(trifluoromethyl)-1-pyrrolidinyl]-2-pyrimidinamine (600 mg, 2.138 mmol) and (4-cyano-3,5-difluorophenyl)boronic acid (587 mg, 3.21 mmol) were dissolved in 1,4-dioxane (10 mL) in a 20 mL sealable vial. Saturated NaHCO3 solution (5 mL) was added, and N2 gas was bubbled through the mixture for 10 minutes. Then Pd(Ph3P)4 (371 mg, 0.321 mmol) was added, and N2 gas was bubbled through the mixture for an additional 5 minutes. The reaction vial was then capped and heated at 100° C. overnight. The reaction was diluted with water (10 mL) and then extracted with EtOAc (3×10 mL). Organic was then combined, dried over MgSO4, filtered and concentrated. The yellow oil was then purified on Biotage SNAP 50 g column with a gradient of 0 to 35% EtOAc in Hexane over 30 minutes to isolated the title compound (452 mg). LC-MS (ES) m/z=384 [M+H]+.

Provenance & Evidence