Triphenylphosphine → HCID 53899586, compound

HRID 564014Notes

Reaction equation

HRID 564014 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[C:8]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])[CH:9]=[CH2:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[C:13]([O:12][C:8](=[O:11])[CH:9]=[CH:10][C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 15458tert-Butyl acrylateHCID 783445-Bromopyrimidine

Product 1

HCID 53899586HCID 53899586, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

4.25 g 5-bromopyrimidine, 8.83 g tert.-butyl acrylate, 900 mg palladium (II) acetate, 1.79 g triphenylphosphane and 351 mg triethylamine were charged to a closed glass vial and heated with stirring to 80° C. over night. The mixture was evaporated under vacuum, the residue dissolved in ethyl acetate and filtered over a pad of silica. The filtrate was evaporated to yield 2.0 g of crude 3-pyrimidin-5-yl-acrylic acid tert.-butyl ester.

Workup

  1. temperatureheated
  2. customThe mixture was evaporated under vacuum
  3. dissolutionthe residue dissolved in ethyl acetate
  4. filtrationfiltered over a pad of silica
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5f8e387749584e9ba7de0820eb79e43a
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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