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

HRID 2117611Notes

Reaction equation

HRID 2117611 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 16 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 on silica gel (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 16 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 on silica gel (10% to 30% hexanes in EtOAc)

Sources & evidence

ORD record
ord-700e54040c194488a267342e7e287f7a
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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