Potassium Hydroxide → tert-Butyl (2-(1,8-naphthyridin-2-yl)ethyl)carbamate

HRID 379233Notes

Reaction equation

HRID 379233 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][C:10](=O)[CH3:11])([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[C:20]([CH:21]=O)=[CH:19][CH:18]=[CH:17][N:16]=1.[OH-].[K+]>C(O)C>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 12111481tert-butyl N-(3-oxobutyl)carbamate

Product 1

HCID 53952251tert-Butyl (2-(1,8-naphthyridin-2-yl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10-4 (10 g, 53.4 mmol), 2-amino-3-formylpyridine 1-3 (7.2 g, 64 mmol), 20% aq. KOH (1 mL), and ethanol (200 mL) was heated at reflux for 3 h. Evaporation of the solvents and flash chromatography (silica, 70 CHCl3/28 EtOAc/2 MeOH) gave 10-5 as a solid.

Workup

  1. temperatureat reflux for 3 h
  2. customEvaporation of the solvents and flash chromatography (silica, 70 CHCl3/28 EtOAc/2 MeOH)

Sources & evidence

ORD record
ord-d38972e01f11444a95781bb690afaf08
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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