3-PYRIMIDIN-5-YL-BENZOIC ACID

General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 °C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product.3-(4.4, 5.5-Tetramethyl-1 , 3, 2-dioxaborolan-2-yl)benzoic acid (496 mg, 2.00 mmol), 5- bromopyrimidine (382 mg, 2.40 mmol), PdC (dppf) DCM complex (82 mg, 5 molpercent) were stirred in 1 , 4-dioxane (10 mL) under nitrogen and a solution of potassium carbonate (829 mg, 6.00 mmol) in water (5 mL) was added. The mixture was degassed with a stream of nitrogen bubbles and heated in the microwave (120 C/30 minutes). The volatiles were removed in vacuo and the aqueous residue diluted with water (50 mL) and DCM (50 mL). The mixture was filtered through celite, the DCM phase discarded and the aqueous phase extracted with further DCM (2 50 mL). The DCM extracts were again discarded, the aqueous phase was adjusted to pH 3 with 30percent w/v aqueous NaHSCU and the precipitate collected by filtration and dried under vacuum (40 C/3 hours over P2O5) to give the desired compound (137 mg, 34percent yield) as a grey solid. LCMS-B: RT 3.25 min; m/z 201.1 [M+H]

Molecular Weight:200.19
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:200.058577502
Monoisotopic Mass:200.058577502
Topological Polar Surface Area:63.1
Heavy Atom Count:15
Complexity:227
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes