2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine → 6,7,8,9-tetrahydro-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine

HRID 2120798Notes

Reaction equation

HRID 2120798 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:4]2[C:13]3[CH:12]=[CH:11][N:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:14])[C:5]=2[N:15]=1.[H][H]>FC(F)(F)C(O)=O.[Pt]=O>[CH3:1][C:2]1[N:3]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:4]2[C:13]3[CH2:12][CH2:11][NH:10][CH2:9][C:8]=3[N:7]=[C:6]([NH2:14])[C:5]=2[N:15]=1

Participants

5

Reactant 2

HCID 120158092-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 120158106,7,8,9-tetrahydro-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A catalytic amount of platinum oxide was added to a solution of 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine (0.1 g, 0.4 mol) in trifluoroacetic acid. The reaction mixture was reduced on a Parr apparatus at 50 psi (3.5 Kg/cm2) hydrogen pressure overnight. The reaction mixture was filtered and washed with methanol to remove the catalyst, and the filtrate was concentrated under vacuum. The residue was combined with dichloromethane and aqueous sodium bicarbonate was added until the mixture was basic. The dichloromethane layer was separated, and the aqueous layer was extracted three times with dichloromethane (100 mL). The combined dichloromethane extracts were dried over magnesium sulfate and concentrated under vacuum. The resulting residue was recrystallized from toluene to provide 6,7,8,9-tetrahydro-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine as a solid, m.p. 226-230° C. Analysis: Calculated for C14H21N5+1.75 H2O: %C, 57.81; %H, 8.49; %N, 24.07. Found: %C, 57.89; %H, 8.04; %N, 23.45.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated under vacuum
  5. additionwas added until the mixture
  6. customThe dichloromethane layer was separated
  7. extractionthe aqueous layer was extracted three times with dichloromethane (100 mL)
  8. dry with materialThe combined dichloromethane extracts were dried over magnesium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe resulting residue was recrystallized from toluene

Sources & evidence

ORD record
ord-dad2579497814fcd892a8bcd1cfa95c7
Source dataset
uspto-grants-2004_02
Patent number
US06693113B2

Reaction notes

Loading…