5-(1-methyl-1H-pyrazol-5-yl)-2-Pyrimidinecarboxylic acid synthesis

Yield:1067612-22-9 36%

Reaction Conditions:

with potassium carbonate;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in 1,4-dioxane;water at 80; for 12 h;Sealed tube;

Steps:

3.a

Example 3Preparation of /V-(2-amino-1-benzylethyl)-5-(1-methyl-1 H-pyrazol-5-yl)pyrimidine-2- carboxamidea) 5-(1-methyl-1 H-pyrazol-5-yl)pyrimidine-2-carboxylic acidTo a solution of 1-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H- pyrazole (1.35 g, 6.5 mmol) in dioxane/H₂O (5:1 , 59 ml.) was added K₂CO₃ (2.8g, 20.3 mmol), tetrakistriphenylphosphine Pd(O) (340 mg, 0.3 mmol), and 5-bromo-2- pyrimidinecarboxylic acid (1.2 g, 5.9 mmol). The reaction mixture was heated to 80° C in a sealed tube for 12h. The reaction solution was poured onto H₂O (100 ml.) and extracted with DCM. The organics were dried (Na₂SO₄), concentrated under vacuum to give the title compound (0.9 g, 36%) as a tan solid: LC-MS (ES) m/z = 437 (M+H)⁺.

References:

WO2008/121786,2008,A1 Location in patent:Page/Page column 47