4-[(3-Nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol → 4-[(3-Amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol

HRID 1363591Notes

Reaction equation

HRID 1363591 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:22])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[N:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:22])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[N:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 669191374-[(3-Nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol

Product 1

HCID 669191884-[(3-Amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-olYield 115.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[(3-nitro[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol (12.2 g), 5% platinum on carbon (1.22 g), and ethyl acetate (160 mL) was placed under hydrogen pressure (40 psi, 2.8×105 Pa) for 3 hours. The reaction mixture was filtered through a layer of CELITE filter aid and the filter cake was rinsed with 1:1 ethyl acetate:methanol (150 mL). The filtrate was concentrated under reduced pressure to provide 12.66 g of 4-[(3-amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol as a thick semi-solid.

Workup

  1. customfor 3 hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was rinsed with 1:1 ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f03c09b94b64ae994eb3c12e281f284
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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