Binap, (A+-)- → 2-(4-tert-Butylthiazol-2-ylamino)-6-(3-acetamidophenyl)pyrazine

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Reaction Steps

Following Method L, 2-(3-acetamidophenyl)-6-chloropyrazine (4a) (60 mg, 0.24 mmol), 4-(tert-butyl)-1,3-thiazol-2-amine (54.7 mg, 0.35 mmol), Pd(0)2 dba3 (9 mg, 0.01 mmol), BINAP (50 mg, 0.04 mmol), sodium tert-butoxide (33 mg, 0.34 mmol) and toluene (5 mL) were reacted at 85° C. for 16 hours. The same workup as is Method L produced a solid that was washed with 50 mL dichloromethane and filtered. The dichloromethane slowly evaporated to produce white crystals that were removed by filtration and washing with dichloromethane (10 mL). The dichloromethane was then evaporated and the resulting crude was chromatographed in silica gel using ethyl acetate: dichloromethane, 2:1, as eluent to furnish 18.5 mg of title compound. Yield: 21.0%. 1 H NMR (250 MHz, DMSO-d6) δ 1.30 (s, 9H), 2.10 (s, 3 H), 6.69 (s, 1 H), 7.47 (t, 1 H, 7.9 Hz), 7.69 (d, 1 H, 8.0 Hz), 7.89 (d, 1 H, 7.8 Hz), 8.38 (s, 1 H), 8.45 (bs, 1 H), 8.58 (s, 1 H), 10.11 (s, 1 H), 11.78 (bs, 1 H);

Provenance & Evidence