Sodium borohydride → 6-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

HRID 1774798Notes

Reaction equation

HRID 1774798 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13][C:12]=3[N:11]=2)[CH:7]=[N:6][CH:5]=1.[BH4-].[Na+]>CO>[OH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13]3)[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866791615-(5-Methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester

Product 1

HCID 866791626-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-oneYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-(5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester (270 mg, 0.91 mmol) in MeOH (10 mL) was added sodium borohydride (300 mg, 8.0 mmol) at RT. After stirring overnight, the reaction mixture was quenched by adding water (5.0 mL). It was then concentrated in vacuo to give a light yellow oil. After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 6-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one (190 mg, 77.6%) as a white solid. MS: 270.1 (M+H+).

Workup

  1. customthe reaction mixture was quenched
  2. additionby adding water (5.0 mL)
  3. concentrationIt was then concentrated in vacuo
  4. customto give a light yellow oil
  5. extractionAfter extraction with EtOAc
  6. washthe organic layer was washed with brine
  7. customdried over anhy
  8. filtrationNa2SO4, filtered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4da4bbcca8cb4bd9b732b932010d8649
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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