Ethanol → 5-(4-Formylphenyl)pyrimidine

HRID 50560

Reaction equation

HRID 50560 reaction equation
C([O-])([O-])=O.[Na+].[Na+].C(O)C.Cl.Cl[C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19]>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>[N:14]1[CH:13]=[C:12]([C:23]2[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=2)[CH:17]=[N:16][CH:15]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 227351705-Chloropyrimidine hydrochloride

Product 1

HCID 38612125-(4-Formylphenyl)pyrimidineYield 48.7%

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 5-chloropyrimidine hydrochloride (3.03 g, 20.06 mmol, prepared as described in WO 9821188), 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 185 (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-ae4430c86d0f46dba2137ba2e4b21c4e
Source dataset
uspto-grants-2004_03
Patent number
US06713455B2

Linked notes

Loading…