2,5-Dichloropyrimidine → HCID 86664881, compound

HRID 2042679Notes

Reaction equation

HRID 2042679 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Cl[C:13]1[N:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=1>C1(C)C=CC=CC=1.C(O)C>[Cl:19][C:16]1[CH:15]=[N:14][C:13]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)=[N:18][CH:17]=1

Participants

5

Reactant 2

HCID 5906412,5-DichloropyrimidineHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 86664881HCID 86664881, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Palladium dichloro-bis(triphenylphosphine) (3.5 g) was added to a stirred solution of 4-formylbenzene boronic acid (32.5 g), 2,5-dichloro-pyrimidine (30 g) in toluene (1000 ml) and ethanol (100 ml) under an argon atmosphere. The solution was purged with argon and aqueous sodium carbonate (2N) (200 ml) was added. The reaction mixture was stirred at 60° C. for 90 minutes, cooled to ambient temperature, diluted with ethyl acetate, and washed successively with aqueous sodium hydrogen carbonate (saturated), water and brine. The combined organic extracts were treated with charcoal, dried over sodium sulfate, filtered through Hyflo® and concentrated in vacuo. The residue was triturated with diethyl ether (100 ml), the solid isolated by filtration and dried under high vacuum to give 4-(5-chloro-pyrimidin-2-yl)-benzaldehyde as a white solid. M.p. 186° C. 1H NMR (400 MHz, DMSO) 8.10 (d, 2H), 8.55 (d, 2H), 9.1 (s, 2H).

Workup

  1. customThe solution was purged with argon and aqueous sodium carbonate (2N) (200 ml)
  2. additionwas added
  3. temperaturecooled to ambient temperature
  4. additiondiluted with ethyl acetate
  5. washwashed successively with aqueous sodium hydrogen carbonate (saturated), water and brine
  6. additionThe combined organic extracts were treated with charcoal
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered through Hyflo®
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with diethyl ether (100 ml)
  11. customthe solid isolated by filtration
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-cc6193f3c2c44ec5a54f6ccf6716fd1b
Source dataset
uspto-grants-2013_11
Patent number
US08586593B2

Reaction notes

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