Dimethylformamide → 5-(4-Formylphenyl)pyrimidine

HRID 1459634Notes

Reaction equation

HRID 1459634 reaction equation
C[N:2]([CH:4]=O)[CH3:3].[CH:6]([C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)=[O:7].BrC1C=[CH:20][CH:21]=[N:22]C=1>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[N:2]1[CH:3]=[C:20]([C:11]2[CH:12]=[CH:13][C:8]([CH:6]=[O:7])=[CH:9][CH:10]=2)[CH:21]=[N:22][CH:4]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 122863-BromopyridineHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 38612125-(4-Formylphenyl)pyrimidine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of Pd(OAc)2 (0.17 mmol, 38 mg), bisdiphenylphosphinoferrocene (DPPF, 0.23 mmol, 125 mg), and DMF were heated to 50° for 15 minutes. The reaction mixture was cooled. 4-Formyl-benzeneboronic acid (6.93 mmol, 1.0 g), 5-bromopyridine (6.3 nunol, 1.0 g), and Net3 (8.2 mmol; 1.11 mL) were added and the reaction mixture was heated to 90° overnight. The reaction mixture was concentrated to yield a gummy oil. Flash chromatography (EtOAc) yielded 1-3 contaminated with a small amount of 1-1. The tan solid was taken up in EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried (MgSO4), filtered and concentrated to afford the title compound as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperaturethe reaction mixture was heated to 90° overnight
  3. concentrationThe reaction mixture was concentrated
  4. customto yield a gummy oil
  5. washwashed with saturated NaHCO3 and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-efc6b7f072ed44e698e99256eaac8dc7
Source dataset
uspto-grants-1998_12
Patent number
US05854264

Reaction notes

Loading…