Diisopropylethylamine → HCID 86712743, compound

A suspension of 1-(5-aminopyridin-2-yl)ethanone (2.08 g, 15.3 mmol) in DMF (30 mL) and DIPEA (6.65 mL, 38.2 mmol) was stirred at room temperature for 15 minutes. 2,4-Dichloro-5-(trifluoromethyl)pyrimidine (2.47 mL, 18.33 mmol) was added in 4 portions over 5 minutes. The reaction mixture was stirred at 60° C. for 2 hours under a nitrogen atmosphere before it was diluted with water and EtOAc. The aqueous was extracted several times with EtOAc and the combined organic phases were washed with water, brine, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was adsorbed onto silica gel and purified by column chromatography (CombiFlash Rf, 40 g SiO2 Cartridge, 0-30% EtOAc in cyclohexane) to give 2.17 g of a white solid. The 1:1 regiosiomeric mixture was dissolved in a minimum volume of cold (5° C.) acetonitrile (4-8 mL), sonicated for 10 seconds then filtered and dried to give the title compound (A141) as a white solid (1.14 g, 23%). LCMS-B: rt 7.34 min; m/z 317 [M+H]+.

1. stirringThe reaction mixture was stirred at 60° C. for 2 hours under a nitrogen atmosphere before it
2. extractionThe aqueous was extracted several times with EtOAc
3. washthe combined organic phases were washed with water, brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. customthe solvent evaporated in vacuo
7. custompurified by column chromatography (CombiFlash Rf, 40 g SiO2 Cartridge, 0-30% EtOAc in cyclohexane)

ORD record

ord-fc7c5d732afd43c1b41e872689e07d98

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266864B2