HCID 67521556, compound → HCID 86643248, compound

HRID 1924032Notes

Reaction equation

HRID 1924032 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[N:15]=[CH:14][C:13]=1[N+:22]([O-])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(#N)C.[Pt]>[Si:1]([O:8][CH2:9][CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[N:15]=[CH:14][C:13]=1[NH2:22])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67521556HCID 67521556, compound

Product 1

HCID 86643248HCID 86643248, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

N-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-3-nitro[1,5]naphthyridin-4-amine (2.36 g, 6.78 mmol) was dissolved in 50 mL of acetonitrile and the solution was placed in a pressure bottle. Platinum on carbon (5%, 200 mg) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 3 hours, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with acetonitrile and the combined filtrates were concentrated under reduced pressure to give 2.12 g of N4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)[1,5]naphthyridine-3,4-diamine as an orange solid.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with acetonitrile
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-23b4fcea737849fb9ad47e7bfc86f5bb
Source dataset
uspto-grants-2012_05
Patent number
US08178539B2

Reaction notes

Loading…