Benzylamine → 2-(benzylamino)-5-bromo-3-methylpyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-chloro-3-methylpyrimidin-4(3H)-one (Example 143, Step B, 0.100 g, 0.448 mmol), phenylmethanamine (0.064 ml, 0.582 mmol) and NaHCO3 (0.150 g, 1.79 mmol) in n-BuOH (3 mL) was stirred at 60° C. for 4 hours. The reaction mixture was cooled to room temperature and then diluted with EtOAc. The EtOAc layer was washed with H2O and saturated aqueous NaCl. The aqueous phase was re-extracted with EtOAc (1×). The combined EtOAc layers were dried (Na2SO4), filtered and concentrated to yield the desired product (0.130 g, 99%) as a pale yellow solid that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.96 (t, 1H), 7.90 (s, 1H), 7.32 (s, 2H), 7.31 (m, 2H), 7.23 (m, 1H), 4.57 (d, 2H), 3.39 (s, 3H). LRMS (ESI pos) m/e 294, 296 (M+, Br pattern).

Provenance & Evidence