2-Bromopyrimidine → 4-(Pyrimidin-2-yl)benzaldehyde

HRID 1595906Notes

Reaction equation

HRID 1595906 reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:8]([C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1)=[O:9].C(=O)(O)[O-].[Na+]>COCCOC.O.C(Cl)Cl>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[C:13]1[CH:14]=[CH:15][C:10]([CH:8]=[O:9])=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 783452-BromopyrimidineHCID 516892Sodium BicarbonateHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 127037224-(Pyrimidin-2-yl)benzaldehydeYield 84.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-bromopyrimidine (1.00 g, 6.3 mmol) and tetrakistriphenylphosphine(0) palladium (0.218 g, 0.189 mmol) in ethylene glycol dimethyl ether (30 mL) was stirred at room temperature for 10 minutes. A solution of 4-formylbenzene boronic acid (1.14 g, 7.61 mmol) and sodium bicarbonate (1.58 g, 18.9 mmol) in 15 mL water was added and the reaction was heated at reflux for 18 h. The mixture was diluted with water and CH2Cl2. The layers were separated, and the aqueous solution was washed with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography (10% to 30% hexanes in EtOAc) to afford the title compound (0.979 g). 1H NMR (400 MHz, CDCl3) δ 10.11 (s, 1H), 8.83 (s, 2H), 8.82 (s, 1H), 7.98 (s, 2H), 7.23 (s, 2H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 18 h
  3. customThe layers were separated
  4. washthe aqueous solution was washed with CH2Cl2
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via flash chromatography (10% to 30% hexanes in EtOAc)

Sources & evidence

ORD record
ord-2d07b3d6a59f4a9faf8037ab0d131bcd
Source dataset
uspto-grants-2001_09
Patent number
US06288120B1

Reaction notes

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