2-[2-(3-Chloro-phenylethynyl)-pyrimidin-4-yl]-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester → 2-[2-(3-Chloro-phenylethynyl)-pyrimidin-4-yl]-1-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 869334Notes

Reaction equation

HRID 869334 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:32])[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]#[C:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=4)[N:18]=3)=[CH:16][C:10]=2[C:9]1=[O:33])=O)(C)(C)C>Cl.O1CCOCC1>[Cl:31][C:27]1[CH:26]=[C:25]([C:24]#[C:23][C:19]2[N:18]=[C:17]([C:15]3[N:14]([CH3:32])[C:11]4[CH2:12][CH2:13][NH:8][C:9](=[O:33])[C:10]=4[CH:16]=3)[CH:22]=[CH:21][N:20]=2)[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 672847722-[2-(3-Chloro-phenylethynyl)-pyrimidin-4-yl]-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 672857682-[2-(3-Chloro-phenylethynyl)-pyrimidin-4-yl]-1-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 50%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 2-[2-(3-chloro-phenylethynyl)-pyrimidin-4-yl]-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.018 g, 0.05 mmol) in 4M HCl in dioxane (3.0 ml) was stirred at room temperature for 2 h. The solvent was removed under vacuum and the crude was purified by column chromatography over silica gel, using DCM/MeOH (9.8:0.2) as eluent, affording 2-[2-(3-Chloro-phenylethynyl)-pyrimidin-4-yl]-1-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one as a yellow solid (0.007 g, 0.02 mmol, 50%).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe crude was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-20504054f2694e5e97f5c54eb846b958
Source dataset
uspto-grants-2015_03
Patent number
US08969366B2

Reaction notes

Loading…