1-(6-Chloropyrimidin-4-yl)ethan-1-one → 2-(6-Chloropyrimidin-4-yl)propan-2-ol

Temperature

0 °C

To a stirred solution of 1-(6-chloro-4-pyrimidinyl)ethanone (Intermediate 18, 500 mg, 3.19 mmol)) in THF (5 mL) was added methylmagnesium bromide (1.171 mL, 3.51 mmol), and the resulting mixture stirred under argon at 0° C. for 2 hrs. The reaction was quenched with water (25 mL) with stirring and extracted with ethyl acetate (50 mL). The combined organic layers were dried (MgSO4), filtered and evaporated to dryness to afford the crude residues. Crude residues were then purified on Biotage Isolera on a pre-packed silica cartaridge (25 g) eluting with 0-20% ethyl acetate-isohexane. The appropriate fractions were combined and evaporated in vacuo to give the required product as a yellow oil (218 mg).

1. customThe reaction was quenched with water (25 mL)
2. stirringwith stirring
3. extractionextracted with ethyl acetate (50 mL)
4. dry with materialThe combined organic layers were dried (MgSO4)
5. filtrationfiltered
6. customevaporated to dryness
7. customto afford the crude residues
8. customCrude residues were then purified on Biotage Isolera on a pre-packed silica cartaridge (25 g)
9. washeluting with 0-20% ethyl acetate-isohexane
10. customevaporated in vacuo

ORD record

ord-e9ad778e58ca4871a677c206283c18ed

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796283B2