HCID 71240815, compound → HCID 71241153, compound

HRID 1774608Notes

Reaction equation

HRID 1774608 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8]([C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([Cl:26])[CH:17]=3)[N:13]=[CH:12][N:11]=2)=[CH:7][N:6]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:4]>[Pd].CCOC(C)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([Cl:26])[CH:17]=3)[N:13]=[CH:12][N:11]=2)[CH2:7][N:6]1[C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])=[O:4]

Participants

4

Reactant 1

HCID 71240815HCID 71240815, compound

Product 1

HCID 71241153HCID 71241153, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on carbon (0.22 g, 0.21 mmol) was added in one portion to a stirred solution of 4-[6-(3-chloro-4-isopropoxy-phenyl)-pyrimidin-4-yl]-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.03 g, 0.06 mmol) in EtOAc (15 ml) and the mixture was stirred at room temperature under a hydrogen atmosphere for 24 hours. After this time, the mixture was filtered through celite and the resulting filtrate concentrated to give the title compound (0.03 g, 22% yield) as a colourless oil. Tr=2.61 min m/z (ES+) (M+H+) 476.

Workup

  1. filtrationAfter this time, the mixture was filtered through celite
  2. concentrationthe resulting filtrate concentrated

Sources & evidence

ORD record
ord-4c95f4a5d63e4d7b9cbd24c07ecb5079
Source dataset
uspto-grants-2016_02
Patent number
US09260422B2

Reaction notes

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