(+)-9-{6-[(4-Methoxy-benzyl)-methyl-amino]-pyridin-2-yl}-3-pyrimidin-5-yl-non-4-enoic acid ethyl ester → (+)-9-{6-[(4-Methoxy-benzyl)-methyl-amino]-pyridin-2-yl}-3-pyrimidin-5-yl-nonanoic acid ethyl ester

HRID 860060Notes

Reaction equation

HRID 860060 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][CH:6]([C:30]1[CH:31]=[N:32][CH:33]=[N:34][CH:35]=1)[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH3:20])[N:14]=1)[CH3:2].[H][H]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:36])[CH2:5][CH:6]([C:30]1[CH:31]=[N:32][CH:33]=[N:34][CH:35]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH3:20])[N:14]=1)[CH3:2]

Participants

5

Reactant 2

HCID 69665963(+)-9-{6-[(4-Methoxy-benzyl)-methyl-amino]-pyridin-2-yl}-3-pyrimidin-5-yl-non-4-enoic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 69666640(+)-9-{6-[(4-Methoxy-benzyl)-methyl-amino]-pyridin-2-yl}-3-pyrimidin-5-yl-nonanoic acid ethyl esterYield 73.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-11 (1.23 g, 2.51 mmol) and 10% Pd/C (0.200 g) in EtOH (25 mL) was stirred under a balloon of hydrogen for 2 days. Filtration through celite and evaporative removal of the solvent followed by purification on silica gel (70:25:5 CHCl3:EtOAc:MeOH) afforded 0.900 g of 6-12.

Workup

  1. filtrationFiltration through celite
  2. customremoval of the solvent
  3. customfollowed by purification on silica gel (70:25:5 CHCl3:EtOAc:MeOH)

Sources & evidence

ORD record
ord-1c22a70c377243c5a8f0ef383bdf6ed1
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

Loading…