1,2-Dimethoxyethane → HCID 59840903, compound

HRID 1890972Notes

Reaction equation

HRID 1890972 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O)[CH3:10].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:1][C:2]1[CH:7]=[C:6]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 709434,6-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 2734902(2-Ethoxyphenyl)boronic acid

Product 1

HCID 59840903HCID 59840903, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

To a solution of 4,6-dichloropyrimidine (6.0 g, 0.04 mol) and 2-ethoxyphenylboronic acid (4.81 g, 0.029 mol) in mixture of dimethoxyethane (120 mL) and water (18 mL) were added NaHCO3 (6.72 g, 0.08 mol) and (PPh3)2PdCl2 (0.84 g) and the reaction mixture was allowed to reflux for 8 h, then it was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL), the resulting solution was washed with water (20 mL), dried over anhydrous K2CO3, filtered and the solvent removed under reduced pressure. The crude product was purified by flash chromatography on silica (eluent CH2Cl2) and recrystallized from hexanes. Yield of 4-chloro-6-(2-ethoxyphenyl)-pyrimidine 4.97 g (73%).

Workup

  1. temperatureto reflux for 8 h
  2. concentrationit was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  4. washthe resulting solution was washed with water (20 mL)
  5. dry with materialdried over anhydrous K2CO3
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe crude product was purified by flash chromatography on silica (eluent CH2Cl2)
  9. customrecrystallized from hexanes

Sources & evidence

ORD record
ord-e021442e31e941d4b229242b536ecb63
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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