Benzenamine, 3-(4-pyrimidinyl)- (9CI) synthesis

Yield:16496-10-9 100 mg

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen;sodium acetate in water;ethyl acetate; for 6 h;

Steps:

26 [000314] Synthesis of 3-(pyrimidin-4-yl) aniline (386)

[000314] Synthesis of 3-(pyrimidin-4-yl) aniline (386): To a stirred solution of compound385 (200 mg, crude) in EtOAc (50 mL) under inert atmosphere were added sodium acetate (304mg, 3.71 mmol), 10% Pd/C (100 mg, wet) under argon atmosphere and stirred under H2atmosphere (balloon pressure) for 6 h. After completion of the reaction, the reaction mixture wasfiltered through celite, washed with 50% MeOH/ CH2C12 (50 mL). The filtrate was concentratedin vacuo to obtain the crude which was purified through silicagel column chromatography in90% EtOAc/ hexanes to afford compound 386 (100 mg, 78%) as an off-white solid. TLC: 70%% EtOAc/ hexanes (R 0.4); 1H NMR (400 MHz, DMSO-d6): ? 9.19 (s, 1H), 8.80 (d, J 5.4Hz, 1H), 7.91 (dd, J= 5.4, 1.4 Hz, 1H), 7.45-7.43 (m, 1H), 7.30 (d, J 7.7 Hz, 1H), 7.18 (t, J7.8 Hz, 1H), 6.74 (d,J 7.5 Hz, 1H), 5.31 (s, 2H).

References:

WO2015/138895,2015,A1 Location in patent:Paragraph 000314