Isobutyraldehyde → HCID 21946010, compound

A solution of diisopropylamine (1.1 mL; 7.85 mmol) (Aldrich) and freshly distilled tetrahydrofuran (15 mL) was cooled to −78° C. n-Butyllithium (2.5M in hexanes; 3.1 mL; 7.75 mmol) (Aldrich) was added dropwise and stirring continued for 40 minutes to prepare a LDA solution. 2,4-Dichloropyrimidine (0.50 g; 3.37 mmol) (Aldrich) in tetrahydrofuran (3 mL) was then added dropwise to this freshly prepared LDA solution over 15 minutes. After stirring for 40 minutes, isobutyraldehyde (0.61 mL; 6.72 mmol) (Aldrich) was added over 6 minutes and stirring continued for another 30 minutes. The reaction was quenched with the addition of 25% aqueous ammonium chloride solution (20 mL) and then diluted with ethyl acetate and water. The organic phase was washed with a second portion of aqueous ammonium chloride solution and then brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Biotage 40S; 10:90 to 15:85 ethyl acetate-hexanes gradient) to give (±)-1-(2,4-dichloro-pyrimidin-5-yl)-2-methyl-propan-1-ol. (Yield 0.25 g; 33.4%).

1. additionwas added dropwise
2. stirringAfter stirring for 40 minutes
3. stirringstirring
4. waitcontinued for another 30 minutes
5. customThe reaction was quenched with the addition of 25% aqueous ammonium chloride solution (20 mL)
6. additiondiluted with ethyl acetate and water
7. washThe organic phase was washed with a second portion of aqueous ammonium chloride solution
8. dry with materialbrine, dried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by flash chromatography (Biotage 40S; 10:90 to 15:85 ethyl acetate-hexanes gradient)

ORD record

ord-5f057ae64a2b480d9faaada3e4e13183

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07112676B2