(E)-2-Methoxy-4-styrylpyrimidine → HCID 58093434, compound

HRID 475000Notes

Reaction equation

HRID 475000 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][N:4]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 58093422(E)-2-Methoxy-4-styrylpyrimidine

Product 1

HCID 58093434HCID 58093434, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-2-methoxy-4-styrylpyrimidine (0.51 g, 2.4 mmol) in methanol (25 mL) was added palladium on carbon (0.18 g). The reaction mixture was stirred under hydrogen balloon for 3 days and then filtered through a pad of celite. The filtrate was concentrated under reduced pressure to provide the title compound (0.50 g, 97%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 8.35 (d, J=5.0 Hz, 1H), 7.29-7.26 (m, 2H), 7.21-7.18 (m, 3H), 6.72 (d, J=5.0 Hz, 1H), 4.02 (s, 3H), 3.08-2.98 (m, 4H).

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-32d0a202e8864127bf2451e775911a56
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

Loading…