1,2-Dimethoxyethane → 4-Chloro-2-methyl-6-phenylpyrimidine

HRID 1592245Notes

Reaction equation

HRID 1592245 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Ba+2].[OH-].COCCOC.[CH3:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[C:22]([Cl:27])[N:21]=1>O>[CH3:19][C:20]1[N:21]=[C:22]([Cl:27])[CH:23]=[C:24]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:25]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 6093286Barium hydroxide

Product 1

HCID 7961284-Chloro-2-methyl-6-phenylpyrimidineYield 51.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A reaction vessel was charged with 2.19 g of tetrakistriphenylphosphine palladium, 847 mg of phenylboronic acid, and 2.99 g of barium hydroxide, to which 40 ml of 1,2-dimethoxyethane, 7 ml of water, and 1.01 g of 2-methyl-4,6-dichloropyrimidine were added, followed by stirring at 80° C. under an atmosphere of a nitrogen gas for 6 hours. The reaction mixture was then left for cooling to room temperature, and water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.65 g of 2-methyl-4-chloro-6-phenylpyrimidine.

Workup

  1. additionwere added
  2. waitThe reaction mixture was then left
  3. temperaturefor cooling to room temperature
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ef88dd024d1a490999d163f7842037b3
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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