3-Methylbutanal → HCID 86667308, compound

Temperature

-78 °C

To a solution of 5-bromo-2-chloropyrimidine (5.0 g, 25.8 mmol) in diethyl ether (129 mL) and THF (129 mL) was added isovaleraldehyde (4.45 g, 51.7 mmol). The reaction mixture was cooled to −78° C., and n-butyllithium (15.4 mL of a 1.6 M solution in hexanes, 24.6 mmol) was added. The mixture was stirred for 30 m at −78° C. The reaction mixture was quenched by addition of saturated aqueous NH4Cl, and extracted with ethyl acetate (300 mL×3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give 1-(2-chloropyrimidin-5-yl)-3-methylbutan-1-ol (1.98 g) as yellow oil. 1HNMR (400 MHz, CDCl3) δ 8.54 (s, 2H), 4.76-4.80 (m, 1H), 1.75-1.66 (m, 2H), 1.45-1.37 (m, 1H), 0.89 (d, J=6.35 Hz, 6H).

1. customThe reaction mixture was quenched by addition of saturated aqueous NH4Cl
2. extractionextracted with ethyl acetate (300 mL×3)
3. dry with materialThe combined organic layers were dried over Na2SO4
4. concentrationconcentrated under reduced pressure

ORD record

ord-d687c78e95fd4c409aea79c144a938de

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809342B2