Triphenylphosphine → HCID 59026710, compound

HRID 606061Notes

Reaction equation

HRID 606061 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH:21]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]3N=N[N:17]=[C:9]3[C:8]=2[N:18]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH:21]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 67041292HCID 67041292, compound

Product 1

HCID 59026710HCID 59026710, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 8-(ethoxymethyl)-5,6-dimethyl-7-[(3-pyridin-3-ylisoxazol-5-yl)methyl]-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridine (0.1712 g, 0.423 mmol) and triphenylphosphine (0.120 g, 0.466 mmol) in toluene (2 mL) was heated at reflux for five days. The solvent was removed and the resulting brown solvent was dissolved in 1 M hydrogen chloride in methanol (5 mL). The solution was heated at reflux for four hours and then concentrated to an oil. The oil was dissolved in hot water. A precipitate formed and was isolated by filtration. The filtrate was washed five times with dichloromethane and then adjusted to pH 14 with 50% (w/w) aqueous sodium hydroxide, resulting in a brown precipitate. The mixture was extracted with several portions of dichloromethane that were combined, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The resulting white solid was triturated with diethyl ether and dried to yield 2-(ethoxymethyl)-6,7-dimethyl-1-[(3-pyridin-3-ylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 189.0-191.0° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for five days
  3. customThe solvent was removed
  4. dissolutionthe resulting brown solvent was dissolved in 1 M hydrogen chloride in methanol (5 mL)
  5. temperatureThe solution was heated
  6. temperatureat reflux for four hours
  7. concentrationconcentrated to an oil
  8. dissolutionThe oil was dissolved in hot water
  9. customA precipitate formed
  10. customwas isolated by filtration
  11. washThe filtrate was washed five times with dichloromethane
  12. customresulting in a brown precipitate
  13. extractionThe mixture was extracted with several portions of dichloromethane that
  14. washwashed with water and brine
  15. dry with materialdried over magnesium sulfate
  16. filtrationfiltered
  17. concentrationconcentrated
  18. customThe resulting white solid was triturated with diethyl ether
  19. customdried

Sources & evidence

ORD record
ord-f1c46025934540d6b48d4949a24c413c
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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