Propanal → HCID 59574716, compound

To 5-bromopyrimidine (2.39 g, 15.0 mmol) and propionaldehyde (1.05 g, 18.0 mmol) in diethyl ether (80 mL), lithium diisopropylamide (18 mmol) in diethyl ether (20 mL) was gradually added dropwise at 0° C. After the dropwise addition, the reaction mixture was warmed to room temperature and stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted by adding water and ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2.5/1) to give a mixture (colorless oil) containing the desired product, which was used for the next step (427 mg, 13% yield). 2-[1-(5-Bromopyrimidin-4-yl)propyl]isoindoline-1,3-dione

1. additionAfter the dropwise addition
2. customAfter completion of the reaction
3. extractionthe reaction mixture was extracted
4. additionby adding water and ethyl acetate
5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
6. customevaporated under reduced pressure
7. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2.5/1)
8. customto give a mixture (colorless oil)

ORD record

ord-73b9cbe4020547aba3cacd83dcf59374

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440666B2