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

HRID 2416542Notes

Reaction equation

HRID 2416542 reaction equation
C([O-])([O-])=O.[Na+].[Na+].C(O)C.Cl[C:11]1[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=1.[OH:19][CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:17]([C:14]1[CH:13]=[N:12][C:11]([C:26]2[CH:27]=[CH:28][C:23](/[CH:22]=[CH:21]/[CH2:20][OH:19])=[CH:24][CH:25]=2)=[N:16][CH:15]=1)[CH3:18]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 35727632-Chloro-5-ethylpyrimidineHCID 22630844[4-[(1E)-3-hydroxy-1-propenyl]phenyl]boronic Acid

Product 1

HCID 22630876(2E)-3-[4-(5-ethyl-2-pyrimidinyl)phenyl]-2-propen-1-olYield 45.3%

Reagents, catalysts & solvents 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-1b89e820f37e4e42983e3709b9d64af8
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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