1,2-Dimethoxyethane → 4-Chloro-6-(2-methoxyphenyl)pyrimidine

HRID 1941909Notes

Reaction equation

HRID 1941909 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.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:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH3:9])[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 709434,6-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 152068354-Chloro-6-(2-methoxyphenyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

To a solution of 4,6-dichloropyrimidine (6.0 g, 40 mmol) and 2-methoxyphenylboronic acid (4.41 g, 29 mmol) in mixture of dimethoxyethane (120 mL) and water (18 mL) were added NaHCO3 (6.72 g, 80 mmol) and (PPh3)2PdCl2 (0.84 g) and the reaction mixture was refluxed for 8 h, and concentrated under reduced pressure. The resulting residue was taken up in CH2Cl2 (100 mL) and the solution washed with water, dried over anhydrous K2CO3, filtered and the solvent removed under reduced pressure. The obtained crude product was purified by flash chropatography on silica (eluent CH2Cl2) and recrystallized from hexanes. Yield of 4-chloro-6-(2-methoxyphenyl)-pyrimidine 4.78 g (75%).

Workup

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

Sources & evidence

ORD record
ord-b84228fece6b41699ba0c4599a7a2102
Source dataset
uspto-grants-2013_03
Patent number
US08389521B2

Reaction notes

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