Methyl acetoacetate → 6-Methyl-2-trifluoromethylpyrimidin-4-ol

To a solution of 2,2,2-trifluoroethanimidamide (3.02 g, 22.9 mmol) and 3-oxobutanoic acid, methyl ester (2.60 mL, 24.0 mmol) in methanol (25 mL) was added 25 wt % sodium methoxide (10.5 mL, 45.8 mmol). The reaction solution was stirred at room temperature overnight. The solvent was removed in vacuo and diluted with ethyl acetate and 5M HCl. The aqueous layer was extracted with ethyl acetate once. The organic solutions were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on a silica gel column to give the desired product as white solid.

1. customThe solvent was removed in vacuo
2. additiondiluted with ethyl acetate and 5M HCl
3. extractionThe aqueous layer was extracted with ethyl acetate once
4. washThe organic solutions were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography on a silica gel column

ORD record

ord-9e17236e3edd4a4d8bda801d283cc8b7

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933085B2