tert-Butyl acrylate → HCID 56974491, compound

HRID 1656448Notes

Reaction equation

HRID 1656448 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]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[N:4]1[CH:3]=[C:2]([C:9](=[CH2:10])[C:8]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 2

HCID 15458tert-Butyl acrylateHCID 783445-Bromopyrimidine

Product 1

HCID 56974491HCID 56974491, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 30 g 5-bromopyrimidine, 1.2 g palladium acetate, 25 mL triethylamine and 250 ml t-butyl acrylate was heated at 80° C. for 5 days. The resulting mixture was concentrated to a waxy solid in vacuo. The residue was taken up in ethyl acetate and filtered. The filtrate was kept in the cold (-20° C., hexane added), and 10.5 g of tan needles deposited: 1H NMR (300 MHz) (d6-DMSO) δ 1.45 (s, 9H), 6.1 (d, 1H, J=12.3 Hz), 6.8 (d, H, J=12.3 Hz), 8.85 (s, 1H), 9.15 (s, 1H); MS (FAB) m/e (MH+): 206.2

Workup

  1. concentrationThe resulting mixture was concentrated to a waxy solid in vacuo
  2. filtrationfiltered
  3. additionThe filtrate was kept in the cold (-20° C., hexane added), and 10.5 g of tan needles

Sources & evidence

ORD record
ord-be4cf37d97b448da9fa7d1e4a996b8e3
Source dataset
uspto-grants-1993_10
Patent number
US05254573

Reaction notes

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