Yield:960297-56-7 35%

Reaction Conditions:

bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran; for 2 h;Heating / reflux;

Steps:

1.A

Methylbenzylzinc chloride (25 ml of 0.5 M THF solution, 12 mmol) was added to a solution of 4,6-dichloro-5-methylpyrimidine (2.0 g, 12 mmol) and bis(triphenylphosphine) palladium(II) chloride (0.4 g. 0.6 mmol) in THF (20 mL). The reaction mixture was heated to reflux for 2 hours, cooled to room temperature, and then poured onto water (10 mL). The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel flash column chromatography (1:10 Et₂O/Hexane) to yield the product (1.0 g, 35%) as a white solid. ¹H NMR (CDCl₃, 400 MHz) δ 8.75 (s, IH), 7.09-7.22 (m, 4H), 6.84 (d, J = 7.81 Hz, IH), 4.15 (s, IH), 2.38 (s, 3H), 2.32 (s, 3H).

References:

WO2007/146824,2007,A2 Location in patent:Page/Page column 64