Methyl Acrylate → HCID 69916936, compound

HRID 2416547Notes

Reaction equation

HRID 2416547 reaction equation
O1CCOCC1.Br[C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][CH:13]=1.CN(C1CCCCC1)C1CCCCC1.[C:34]([O:38][CH3:39])(=[O:37])[CH:35]=[CH2:36]>C(OCC)(=O)C.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].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:39][O:38][C:34](=[O:37])/[CH:35]=[CH:36]/[C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][CH:13]=1

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 24210N-Methyl dicyclohexylamineHCID 312751,4-DioxaneHCID 143877455-Bromo-2-phenylpyrimidine

Product 1

HCID 69916936HCID 69916936, compoundYield 56.1%

Reagents, catalysts & solvents 3

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dioxane (1.3 mL) was added to a mixture of 5-bromo-2-phenylpyrimidine (310 mg, 1.32 mmol, prepared as described in Org. Lett. 2002, 4, 513), tri-t-butylphosphonium tetrafluoroborate (11 mg, 0.038 mmol), and tris(dibenzylideneacetone)dipalladium(0) (18 mg, 0.020 mmol). N-Methyldicyclohexylamine (0.31 mL, 1.45 mmol) and methyl acrylate (0.24 mL, 2.67 mmol) were added and the mixture was stirred for 72 h at room temperature. The mixture was diluted with ethyl acetate, filtered through a small plug of silica gel which was washed with additional ethyl acetate, and the combined filtrates were concentrated. The residue was triturated with 5:1 hexane/ethyl acetate and the solid was filtered and dried in vacuo to provide 178 mg (56%) of the title compound as an off-white solid. MS 241 (M+H)+.

Workup

  1. filtrationfiltered through a small plug of silica gel which
  2. washwas washed with additional ethyl acetate
  3. concentrationthe combined filtrates were concentrated
  4. customThe residue was triturated with 5:1 hexane/ethyl acetate
  5. filtrationthe solid was filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-08cfb4b6343543d9b8c1424b59fbdca3
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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