Water → HCID 131733907, compound

HRID 709728Notes

Reaction equation

HRID 709728 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].C(N(C(C)C)C(C)C)C.O>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:8][C:6]1[N:5]=[C:4]([CH3:9])[N:3]=[C:2]([CH:12]=[CH:11][C:10]([O:14][CH3:15])=[O:13])[CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 81531DiisopropylethylamineHCID 2349974,6-Dichloro-2-methylpyrimidine

Product 1

HCID 131733907HCID 131733907, compoundYield 37.5%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4,6-dichloro-2-methylpyrimidine (2.45 g) and methyl acrylate (3.87 g) in DMF (20 mL) were added tris(dibenzylideneacetone)dipalladium (680 mg), N-ethyldiisopropylamine (3.90 g) and tetrabutylammonium chloride (82 mg) under a nitrogen atmosphere, and the mixture was stirred at 90° C. for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.20 g) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0d9d64640e004261b10fe114c4beb93e
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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