Pyridine → 2-(4-Fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid methyl ester

HRID 1581514Notes

Reaction equation

HRID 1581514 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9](=[O:28])[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)[OH:12]>C(Cl)Cl.CCOCC.[Cr]>[CH3:7][O:8][C:9](=[O:28])[CH:10]([C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)=[O:12]

Participants

6

Reactant 2

HCID 1049PyridineHCID 129914022-(4-Fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-hydroxypropionic acid methyl ester

Product 1

HCID 129914032-(4-Fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid methyl esterYield 43%

Reagents, catalysts & solvents 3

HCID 23976ChromiumCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of CrO3 in CH2Cl2 (300 mL) is added pyridine. The mixture is stirred vigorously for 1 hour at room temp. A solution of the crude 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-hydroxypropionic acid methyl ester, 2, prepared above in CH2Cl2 (50 mL) is added dropwise to the chromium suspension. The reaction mixture is stirred at room temperature for 16 hours, diluted with ether (1 L) and filtered through a pad of Celite. The filtrate is concentrated in vacuo and the resulting residue is purified over silica (25% EtOAc/hexanes) to afford 3.7 g (43% yield) of the desired product as a yellow solid.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 16 hours
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe resulting residue is purified over silica (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-95d5910988fe49288ec27154434697d7
Source dataset
uspto-grants-2004_05
Patent number
US06730668B2

Reaction notes

Loading…