Cesium carbonate → Tert-Butyl 6-((2-tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropyl)methoxy)-2-methylpyrimidin-4-yl((5-methyl-1,3,4-thiadiazol-2-yl)methyl)carbamate

Participants

Reaction Conditions

Reaction Steps

The mixture of 12-6 (160 mg, 0.4421 mmol), tert-butyl (5-methyl-1,3,4-thiadiazol-2-yl)methylcarbamate (122 mg, 0.53 mmol), BINAP (31 mg, 0.049 mmol) and cesium carbonate (173 mg, 0.53 mmol) in toluene (2 mL) was stirred for 5 min before Pd(OAc)2 (10 mg, 0.044 mmol) was added. The mixture was degassed with nitrogen for 5 min, then it was heated to 80° C. for overnight. The solvent was removed under reduced pressure and the residue was purified by Pre-TLC (PE/EA=1/1). The product was obtained as a white solid (120 mg, 49%). 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.39 (d, J=7.9 Hz, 1H), 7.17 (s, 1H), 7.03 (d, J=8.1 Hz, 1H), 5.52 (s, 2H), 4.52-4.18 (m, 2H), 3.64 (dd, J=6.8, 3.6 Hz, 1H), 2.73 (s, 1H), 2.69 (s, 3H), 2.52 (s, 3H), 2.30 (s, 3H), 2.27 (m, 1H), 2.04 (m, 1H), 1.50 (s, 9H), 1.07 (s, 9H); LRMS (ES) calculated M+H for C28H39N6O4S: 555.7. Found: 555.1.

Provenance & Evidence