(3-Benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-methanol → 4-Hydroxymethyl-6-methoxy-[1,5]naphthyridin-3-ol

HRID 1422940Notes

Reaction equation

HRID 1422940 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[CH2:19][OH:20])=[N:16][C:15]([O:21][CH3:22])=[CH:14][CH:13]=2)C1C=CC=CC=1>[Pd].CO>[OH:20][CH2:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:21][CH3:22])[N:16]=2)[N:11]=[CH:10][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 67255949(3-Benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-methanol

Product 1

HCID 1363983214-Hydroxymethyl-6-methoxy-[1,5]naphthyridin-3-olYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on activated carbon (140 mg, 0.13 mmol, 0.1 eq) is added at room temperature to a stirred solution of (3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-yl)-methanol (390 mg, 1.32 mmol, 1.0 eq) in methanol (30 mL). The resulting mixture is stirred under hydrogen flow (4 bars) at room temperature for 1 hour. The catalyst is then removed by filtration and the solution is concentrated to afford 4-hydroxymethyl-6-methoxy-[1,5]naphthyridin-3-ol as a white solid (220 mg, 81% yield).

Workup

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

Sources & evidence

ORD record
ord-59edd523b90f49bb85aa0be0e9408d02
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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