Example 14: Synthesis of ethyl 4-[[(4-methoxyphenyl)methyl]amino]-2-methylthio-5-pyrimidinecarboxylate
To a 60 mL solution of tetrahydrofuran containing ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (6.05 g, 26.07 mmol) was sequentially added triethylamine (11 mL, 79.5 mmol) and 4-methoxybenzylamine (3.6 mL, 27.6 mmol) at room temperature. The reaction mixture was stirred for 1 h. The reaction solution was filtered and the resulting white solid was washed with ethyl acetate. The filtrate and washings were combined and concentrated under reduced pressure. The residue was partitioned between chloroform and saturated aqueous sodium bicarbonate. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give ethyl 4-[[(4-methoxyphenyl)methyl]amino]-2-methylthio-5-pyrimidinecarboxylate (7.60 g, 88% yield) with a melting point of 72-74 °C.
Elemental analysis:
C16H19N3O3S Calculated values: c, 57.64; h, 5.74; n, 12.60.
Measured values: C, 57.65; H, 5.80; N, 12.57.
