Ethanol → (2E)-3-[4-(5-ethyl-2-pyrimidinyl)phenyl]-2-propen-1-ol

1 M aq. Na2CO3 (2 mL), and ethanol (1 mL) were successively added to a mixture of 2-chloro-5-ethylpyrimidine (0.30 mL, 2.47 mmol), [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (61 mg, 0.10 mmol) and [4-[(1E)-3-hydroxy-1-propenyl]phenyl]boronic acid (360 mg, 2.02 mmol, prepared as described in Reference Example 238) in toluene (4 mL) and the resulting mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate (10 mL) and the organic layer was separated, washed with brine (10 mL), dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 3:2 hexane/ethyl acetate) provided 220 mg (45%) of the title compound as a yellow solid. MS 241 (M+H)+.

1. temperaturethe resulting mixture was heated
2. temperatureto reflux for 18 h
3. customThe cooled reaction mixture
4. customthe organic layer was separated
5. washwashed with brine (10 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. customPurification by chromatography (SiO2, 3:2 hexane/ethyl acetate)

ORD record

ord-1b89e820f37e4e42983e3709b9d64af8

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06825170B2