4-Benzylamino-6-methoxy-[1,5]naphthyridin-3-ol → 4-Amino-6-methoxy-[1,5]naphthyridin-3-ol

HRID 1422924Notes

Reaction equation

HRID 1422924 reaction equation
C([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[N:17]=2)[N:12]=[CH:11][C:10]=1[OH:21])C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[N:17]=2)[N:12]=[CH:11][C:10]=1[OH:21]

Participants

4

Reactant 1

HCID 1363447114-Benzylamino-6-methoxy-[1,5]naphthyridin-3-ol

Product 1

HCID 1363447124-Amino-6-methoxy-[1,5]naphthyridin-3-olYield 59%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-benzylamino-6-methoxy-[1,5]naphthyridin-3-ol (50 mg, 0.18 mmol, 1.0 eq) and 70% palladium hydroxide (18 mg, 0.09 mmol, 0.5 eq) in methanol (3 mL) is stirred at room temperature under hydrogen flow (10 bars) for 72 hours. The catalyst is then removed by filtration and the solution is concentrated to afford 4-amino-6-methoxy-[1,5]naphthyridin-3-ol as a grey solid (20 mg, 59% yield) which is directly engaged in the next step.

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-4ece1c47dc2c43ae9918a13ec8ba9fc4
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

Loading…