3-Nitrophenylboronic Acid → HCID 24902113, compound

HRID 1890998Notes

Reaction equation

HRID 1890998 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)([O-:11])=[O:10].C(COC)OC.C([O-])(O)=O.[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:8][C:6]1[CH:7]=[C:2]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:9]([O-:11])=[O:10])[CH:17]=2)[N:3]=[CH:4][N:5]=1

Participants

7

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 80711,2-DimethoxyethaneHCID 709434,6-DichloropyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 24902113HCID 24902113, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

4,6-Dichloropyrimidine (5.58 g, 37.4 mmol) and 3-nitrophenylboronic acid (5.00 g, 27.2 mmol) were added to a stirred mixture of dimethoxyethane (112 mL) and water (17 mL), followed by the addition of NaHCO3 (6.28 g, 75 mmol) and (PPh3)2PdCl2 (0.787 g, 1.12 mmol) herein, and the reaction mixture was refluxed for 8 h. The solvent was removed under reduced pressure. The residue was taken up in CH2Cl2 (100 mL), and the resulting solution washed with water, dried over anhydrous K2CO3, filtered and the solvent removed under reduced pressure. The crude product was purified by column chropatography on silica (eluent CH2Cl2) to yield 4-chloro-6-(3-nitro-phenyl)-pyrimidine (5.52 g; 86%) as yellowish solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 8 h
  2. customThe solvent was removed under reduced pressure
  3. washthe resulting solution washed with water
  4. dry with materialdried over anhydrous K2CO3
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by column chropatography on silica (eluent CH2Cl2)

Sources & evidence

ORD record
ord-bb71631a604148289f2051019392a29a
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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