Boron tribromide → HCID 67160054, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-5-chloro-1-(cyclopropyl-2-methoxyethyl)-3-(6-methoxy-2,5-dimethylpyridin-3-ylamino)pyrazin-2(1H)-one (1.72 g, 4.39 mmol) from Part L in CH2Cl2 (50 mL) at −78° C. was treated with BBr3 (9.65 mL, 9.65 mmol, 1 M in CH2Cl2) dropwise via syringe. After the addition was complete, the reaction mixture was allowed to warm to −40° C., and was stirred at −40 to −35° C. for 45 min. The reaction was quenched by the addition of saturated aqueous NaHCO3. The mixture was then transferred to a separatory funnel containing saturated aqueous NaHCO3 (50 L). The aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified by column chromatography on silica gel (30%→55% ethyl acetate in hexanes) to afford (S)-5-chloro-1-(cyclopropyl-2-hydroxyethyl)-3-(6-methoxy-2,5-dimethylpyridin-3-ylamino)pyrazin-2(1H)-one (1.50 g, 94% yield) as a light yellow amorphous solid: 1H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.87 (s, 1H), 6.89 (s, 1H), 4.07-4.00 (m, 3H), 3.95 (d, J=6.8 Hz, 1H), 3.94 (s, 3H), 2.42 (s, 3H), 2.17 (s, 3H), 1.27-1.23 (m, 1H), 0.83-0.79 (m, 1H), 0.66-0.62 (m, 1H), 0.55-0.51 (m, 1H), 0.35-0.32 (m, 1H); LRMS (ESI) m/e 365.08 [(M+H)+, calcd for C17H22N4O3Cl 365.14].

Provenance & Evidence