Hydrochloric Acid → 4-Pyrimidinecarboxylic acid, 6-methyl-2-(trifluoromethyl)-, ethyl ester

Temperature

2.5 °C

2.241 g (20 mmol) of 2,2,2-trifluoro-acetamidine were dissolved in 80 ml ethanol and treated with 3.163 g (20 mmol) of 2,4-dioxo-pentanoic acid ethyl ester. The resulting solution was cooled to 0-5° C. and treated with 120 ml of HCl-saturated ethanol. The reaction mixture was allowed to warm-up to RT and stirred for additional 3 hours. The mixture was then added dropwise under cooling to 800 ml saturated NaHCO3 solution. The resulting mixture was then extracted twice with 300 ml DCM and the combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo to yield 3.1 g of a yellow oil. This residue was then purified by silicagel chromatography (eluent:heptane/ethyl acetate 100:0 to 30:70) leading to a colorless oil which crystallized spontaneously, leading to 1.3 g of 6-methyl-2-trifluoromethyl-pyrimidine-4-carboxylic acid ethyl ester.

1. temperatureto warm-up to RT
2. additionThe mixture was then added dropwise
3. extractionThe resulting mixture was then extracted twice with 300 ml DCM
4. dry with materialthe combined organic phases were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-55d22c8d6fd644f08315a4bb10965fba

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745477B2