Yield: 90%

Reaction Conditions:

in tetrahydrofuran at 60 - 70; for 3 h;

Steps:

Synthesis of 2-(N-Tert-Butoxycarbonylamino)-3-Methylpyridine (2)
A solution of di-tert-butyl dicarbonate (12.11 g, 55.49 mmol)in tetrahydrofuran (55 mL) was stirred at 60 °C. To thissolution, 2-amino-3-methlypyridine (5 g, 46.24 mmol)was added. The mixture was heated at 70 °C for 3 h and subsequently allowed to cool to room temperature. Theprecipitate was collected by filtration and dried. The rawproduct (8.67 g) was recrystallized from dichloromethane.White crystals suitable for X-ray diffraction analysis wereobtained in a yield of 90%. m.p. 134-138 °C (Lit [16]. m.p.138-140 °C). HRMS (ESI) m/z: calcd for C11N2O2H16[M]+208.0726, found 208.0767. 1H NMR (400 MHz, CDCl3)δ8.27 (d, J = 4.8 Hz, 1H), 7.94 (s, 1H), 7.51 (d, J = 4.4 Hz,1H), 7.02 (dd, J = 7.5, 4.9 Hz, 1H), 2.28 (s, 3H), 1.50 (s,9H). 13C NMR (100 MHz, CDCl3)δ 152.74, 149.91, 145.54,139.56, 126.83, 120.47, 80.29, 28.13, 17.89.

References:

Shi, Yun-Lian;Nie, Xu-Liang;Huang, Tao;Shi, Ming-Zhu;Peng, Da-Yong;Ren, Xue-Xiang;Shi, Xu-Gen;Zhao, Ming-Yu;Li, Bao-Tong [Journal of Chemical Crystallography,2021,vol. 51,# 2,p. 155 - 160]