Water → HCID 131733909, compound

HRID 709731Notes

Reaction equation

HRID 709731 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].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:1][C:2]1[N:3]=[C:4]([O:9][CH3:10])[N:5]=[C:6]([CH:13]=[CH:12][C:11]([O:15][CH3:16])=[O:14])[CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 81531DiisopropylethylamineHCID 120521604,6-Dichloro-2-methoxypyrimidine

Product 1

HCID 131733909HCID 131733909, compoundYield 33.1%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

To a solution of 4,6-dichloro-2-methoxypyrimidine (780 mg) in DMF (10 mL) were added methyl acrylate (760 mg), tris(dibenzylideneacetone)dipalladium (200 mg), N-ethyldiisopropylamine (1.14 g) and tetrabutylammonium chloride (61 mg), 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 (330 mg) 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-61ab2e76f93f4488a56c52d25d496580
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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