Methyl formate → 4-Ethoxy-6-(trifluoromethyl)pyrimidine-5-carbaldehyde

温度

-78 °C

A solution of 5.76 g (21.3 mmoles) of 5-bromo-4-ethoxy-6-trifluoromethylpyrimidine dissolved in 250 ml of THF was cooled to −78° C. Thereto was dropwise added 22.6 ml of n-butyllithium (a 1.6 moles/liter n-hexane solution, 36.1 mmoles). The mixture was stirred for 40 minutes. Thereto was added 2.7 g (45.1 mmoles) of methyl formate. The resulting mixture was stirred for 1.5 hours to give rise to a reaction. After the completion of the reaction, an aqueous ammonium chloride solution was added. The mixture was extracted with diethyl ether. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 3.82 g (yield: 81.6%) of 4-ethoxy-6-trifluoromethylpyrimidine-5-carboaldehyde.

1. stirringThe resulting mixture was stirred for 1.5 hours
2. customto give rise
3. customto a reaction
4. customAfter the completion of the reaction
5. extractionThe mixture was extracted with diethyl ether
6. washThe resulting organic layer was washed with an aqueous sodium chloride solution
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationThe resulting solution was subjected to vacuum distillation
9. customto remove the solvent
10. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

ORDレコード

ord-2e28d0e0e32a4042b32b83d37ecf86d7

出典データセット

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07833939B2