2-(3-Methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester → 2-(3-Methoxypropyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

HRID 1039783Notes

Reaction equation

HRID 1039783 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:18]#[C:19][CH2:20][O:21][CH3:22])=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:10]=1[CH3:11])=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:18][CH2:19][CH2:20][O:21][CH3:22])=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:10]=1[CH3:11])=[O:4]

Participants

4

Reactant 1

HCID 866643322-(3-Methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

Product 1

HCID 866643332-(3-Methoxypropyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylesterYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 500 mg (1.64 mmol) 2-(3-methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester in MeOH (30 ml) was added 170 mg 10%-Pd/C. The reaction solution was stirred under hydrogen atmosphere (balloon) at RT for 16 h. Then the mixture was filtered through celite and the filtrate was concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 480 mg (1.55 mmol, 95%) 2-(3-methoxypropyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

Workup

  1. filtrationThen the mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification of the residue by CC (hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-a2c9542b2c5c45eeb29bad340473e67b
Source dataset
uspto-grants-2013_10
Patent number
US08552200B2

Reaction notes

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