Acetonitrile → Formate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

N-(3-bromo-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine (70 mg, 0.211 mmol), pyrimidin-5-ylboronic acid (52 mg, 0.422 mmol), PdCl2(dppf)-dichloromethane adduct (34.4 mg, 0.042 mmol), and aqueous sodium carbonate (2 M, 211 μL, 0.422 mmol), were suspended in 2-methyltetrahydrofuran (1.05 mL). The vessel was heated to 60° C. for 14 hours. Si-Dimercaptotriazine (222 mg, 0.126 mmol) and acetonitrile (3 mL) were added to the mixture and allowed to stir for 4 hours at room temperature. The reaction mixture was filtered (washing with 1.5 mL DMSO) and concentrated under reduced pressure at 40° C. The mixture was filtered and was purified by mass triggered reverse phase HPLC (57-91% acetonitrile in water+0.1% formic acid) to afford N-(3-methyl-5-pyrimidin-5-ylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine as a formate salt. MS ESI calcd for C16H13F3N5 [M+H]+ 332. found 332. 1H NMR (600 MHz, DMSO-d6) δ 10.28 (s, 1H), 9.16 (s, 1H), 9.03 (s, 2H), 8.81 (d, J=5.2 Hz, 1H), 8.00 (s, 1H), 7.57 (s, 1H), 7.26 (d, J=5.5 Hz, 2H).

Herkunft & Nachweise