Ethanol → 4-(4-Methoxypyrimidin-2-YL)benzaldehyde

HRID 1166089Notes

Reaction equation

HRID 1166089 reaction equation
C([O-])([O-])=O.[Na+].[Na+].C(O)C.Cl[C:11]1[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][N:12]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20]>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>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([C:24]2[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=2)[N:16]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5889352-Chloro-4-methoxypyrimidineHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 226310554-(4-Methoxypyrimidin-2-YL)benzaldehydeYield 42%

Reagents, catalysts & solvents 3

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

Procedure

1 M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of 2-chloro-4-methoxypyrimidine (2.90 g, 20.06 mmol, prepared as described in Tetrahedron 1997, 53, 11595), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.80 g (42%) of the title compound. MS 215 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c7839aee1f174c92b543e0ab98f05371
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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