Trifluoroacetic acid → {2-[4-Ethyl-4-(methoxycarbonyl)piperidin-1-yl]pyrimidin-5-yl}boronic acid

TFA (8 mL) was added to a stirred solution of 1-tert-butyl 4-methyl 4-ethylpiperidine-1,4-dicarboxylate (0.61 g, 2.25 mmol) in 1,4-dioxane (2 mL). The reaction mixture was stirred for 2 h, then the volatiles were removed by rotary evaporation and the residue was left on a high vacuum line for 1 h. The syrupy material thus obtained was dissolved in ethanol (8 mL), anhydrous sodium carbonate (0.72 g, 6.79 mmol) was added and the mixture was stirred for 10 minutes. (2-Chloropyrimidin-5-yl)boronic acid (0.37 g, 2.3 mmol) was added and the mixture was stirred at 80° C. for 7 h. The reaction mixture was filtered through celite, then the solvent was removed under vacuum, and water was added. The mixture was decanted and washed again with water, then the residual gum was freeze-dried, to give the title compound (0.4 g, 60%) as a pale yellow lyophilised solid, which was used without further purification. LCMS (pH 10) MH+ 294, RT 1.15 minutes.

1. customthe volatiles were removed by rotary evaporation
2. waitthe residue was left on a high vacuum line for 1 h
3. customThe syrupy material thus obtained
4. stirringthe mixture was stirred for 10 minutes
5. stirringthe mixture was stirred at 80° C. for 7 h
6. filtrationThe reaction mixture was filtered through celite
7. customthe solvent was removed under vacuum, and water
8. additionwas added
9. customThe mixture was decanted
10. washwashed again with water
11. customthe residual gum was freeze-dried

ORD record

ord-d56f983f50004217acef4b485140d838

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309243B2