Water → HCID 12018702, compound

HRID 1861681Notes

Reaction equation

HRID 1861681 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)=[N+]=[N-].O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 12018701HCID 12018701, compound

Product 1

HCID 12018702HCID 12018702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.1 g (5.9 mmol) 8-azidomethyl-1,6-napthyridine in 20 mL THF was added 2 mL H2O and 3 g PPh3. The resulting solution was alloed to stir overnight at room temperature, then concentrated in vacuo. Purification by flash chromatography (50×140 mm silica gel, linear gradient 5-20% (10% NH4H in MeOH):CH2Cl2) yielded 8-aminomethyl-1,6-napthyridine. 1H NMR (CDCl3, 400 MHz) δ 9.22 (s, 1H); 9.13 (dd, 1H, J=4.3 and 1.8 Hz); 8.70 (s, 1H); 8.32 (dd, 1H, J=8.24 and 1.83 Hz); 7.61 (dd, 1H, J=8.24 and 4.3 Hz); 4.40 (s, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by flash chromatography (50×140 mm silica gel, linear gradient 5-20% (10% NH4H in MeOH):CH2Cl2)

Sources & evidence

ORD record
ord-5fe22f8d03cf4a288ec7fb3781889831
Source dataset
uspto-grants-2003_03
Patent number
US06534510B2

Reaction notes

Loading…