Aminopyrazine → HCID 59436391, compound

Participants

Reaction Steps

To a stirred solution of pyrazin-2-amine (1.626 g, 17.10 mmol) in THF (40 mL) was added isopropylmagnesium chloride (8.44 mL, 16.88 mmol) at 0° C. under N2. The resulting slurry was stirred at RT for 30 min. A solution of (S)-1-tert-butyl 2-methyl azetidine-1,2-dicarboxylate (0.92 g, 4.27 mmol) in THF (5 ml) was added to the reaction slurry. The reaction mixture was stirred at RT for 4 h. and concentrated. The residue was dissolved in EtOAc and washed with 1N HCl, water, and brine. The organic layer was dried over Na2SO4 and filtered. The crude product (1.05 g, 88%) was used in the next step without purification. 1H NMR (400 MHz, MeOD) δ ppm 1.38 (s, 9H) 2.31 (br s, 1H) 2.53 (ddd, J=8.81, 6.17, 2.39 Hz, 1H) 3.89-4.00 (m, 2H) 4.81-4.86 (m, 1H) 8.30-8.37 (m, 2H) 9.41 (s, 1H); LC/MS [M+H]+: 279; Ret time (Method F): 2.27 min.

Provenance & Evidence