HCID 67285360, compound → HCID 67284850, compound

HRID 869329Notes

Reaction equation

HRID 869329 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:33])[C:15]([C:17]3[C:22]([C:23]#[C:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=4)=[CH:21][N:20]=[C:19]([NH2:32])[N:18]=3)=[CH:16][C:10]=2[C:9]1=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:33])[C:15]([C:17]3[C:22]([CH2:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=4)=[CH:21][N:20]=[C:19]([NH2:32])[N:18]=3)=[CH:16][C:10]=2[C:9]1=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67285360HCID 67285360, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67284850HCID 67284850, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[2-Amino-5-(3-hydroxy-phenylethynyl)-pyrimidin-4-yl]-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (obtained as described in Example 9) (25 mg, 0.054 mmol) was dissolved in a methanol (25 mL) and the solution was submitted to continuous hydrogenation in a H-Cube apparatus equipped with a Pd/C 10% cartridge (1 atm of hydrogen, 40° C., flux: 1 mL/min). The solution was then evaporated to dryness and the crude product was purified by chromatography on silica gel (DCM/EtOH 95:5). 2-{2-Amino-5-[2-(3-hydroxy-phenyl)-ethyl]-pyrimidin-4-yl}-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]-pyridine-5-carboxylic acid tert-butyl ester were obtained as a white solid (19 mg, 76%).

Workup

  1. customThe solution was then evaporated to dryness
  2. customthe crude product was purified by chromatography on silica gel (DCM/EtOH 95:5)

Sources & evidence

ORD record
ord-0eada1d350834e54a8ba8b463d90e3e2
Source dataset
uspto-grants-2015_03
Patent number
US08969366B2

Reaction notes

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