The mixture of ethyl 5-((tert-butoxycarbonylamino) methyl)-1,3,4-thiadiazole-2-carboxylate (9-5) (1.0 g, 3.48 mmol), 4-chloro-2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyrimidine (9-6), Pd(OAc)2 (66 mg, 0.29 mmol), BINAP (199 mg, 0.319 mmol) and Cesium carbonate (1.133 g, 3.48 mmol) in toluene (10 mL) was heated to 85° C. under nitrogen for overnight. The solvent was removed under reduced pressure and the residue was purified by chromatography with gradient eluant (PE/EA=10/1; 5/1). The product was obtained as an orange syrup (1.0 g, 63%). 1H NMR (500 MHz, CDCl3) δ 8.26 (s, 1H), 7.35 (dd, J=7.9, 1.8 Hz, 1H), 7.19 (s, 1H), 7.05 (d, J=7.9 Hz, 1H), 5.59 (s, 2H), 4.50 (q, J=7.1 Hz, 2H), 4.35 (m, 2H), 2.53 (s, 3H), 2.27 (s, 3H), 2.13-2.03 (m, 1H), 1.89-1.87 (m, 1H), 1.48-1.43 (m, 12H), 1.32-1.24 (m, 1H), 1.05-1.02 (m, 1H); LRMS (ESI) calculated M+H for C26H32N6O5S: 541.6. Found: 541.2.
