Sodium Bicarbonate → 6-Methoxy-1,5-naphthyridin-3-amine

HRID 1396875Notes

Reaction equation

HRID 1396875 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[NH2:14].C(=O)(O)[O-].[Na+]>CO.[Pd]>[CH3:13][O:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([NH2:14])=[CH:2]2

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 684539634-Bromo-6-methoxy-1,5-naphthyridin-3-amine

Product 1

HCID 667473966-Methoxy-1,5-naphthyridin-3-amineYield 60.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolved 4-bromo-6-(methyloxy)-1,5-naphthyridin-3-amine (as prepared in WO2006081179 A1) (372 mg, 1.464 mmol) in methanol. Added sodium bicarbonate (246 mg, 2.93 mmol) followed by 10% palladium on carbon (312 mg, 0.293 mmol). The mixture was flushed with nitrogen and hydrogenated under balloon pressure for 1 h. After 1 h, filtered reaction mixture and concentrated to afford 155 mg (0.885 mmol, 60%) of the title compound as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) d ppm 4.05 (s, 3H) 6.90 (d, J=9.09 Hz, 1H) 7.38 (br. s., 1H) 8.16 (d, J=8.84 Hz, 1H) 8.54 (br. s., 1H).

Workup

  1. customThe mixture was flushed with nitrogen and hydrogenated under balloon pressure for 1 h
  2. filtrationfiltered
  3. customreaction mixture
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-efe42b51a2de44018d8a67d343360f2a
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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