2-Dimethylamino-pyrimidine-5-boronic acid pinacol ester synthesis

Yield:1032759-30-0 60%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;potassium acetate in 1,4-dioxane;1,2-dimethoxyethane at 150; for 0.25 h;Inert atmosphere;Microwave irradiation;

Steps:

N,N-dimeth l-5-(4,4,5,5-tetrameth l-1,3,2-dioxaborolan-2- l)p rimidin-2-amine (10a)

A mixture of 5-bromo-N,N-dimethylpyrimidin-2-amine (0.966 g, 4.78 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (1.46 g, 5.74 mmol), PdCl2dppf(DCM) (0.114 g, 0.14 mmol) and KOAc (1.407 g, 14.34 mmol) were placed under Ar in a 20 mL microwave flask. Anhydrous 1,2-dimethoxyethane (16 mL) was added and the flask was irradiated at 150 ^oC for 15 minutes. The reaction was filtered through celite, concentrated and slurried in EtOAc. The reaction was filtered through celite again and the organics were concentrated and purified by column chromatography 0 to 30 % EtOAC in Hexanes. The material was isolated as a light teal solid (0.718 g, 60 % yield). ¹H NMR (400 MHz, CDCl₃) δ 8.59 (s, 2H), 3.21 (s, 6H), 1.31 (s, 12H).¹³C NMR (100 MHz, CDCl3) δ 164.1, 83.7, 77.4, 37.2, 25.2, 24.9. HRMS (EI+) m/z calculated for C₁₂H₁₂BN₃O₂ [M+H]⁺: 250.1721, found: 250.17189.

References:

WO2017/197151,2017,A1 Location in patent:Page/Page column 39-40