Triphenylphosphine → HCID 57545330, compound

HRID 2383168Notes

Reaction equation

HRID 2383168 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[CH:15]=3)[N:10]3N=N[N:27]=[C:9]3[C:8]=2[N:28]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[K+]>C(Cl)(Cl)Cl.Cl>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:7]2[C:16]3[CH:15]=[C:14]([O:17][CH2:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:27])[C:8]=2[N:28]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 67229105HCID 67229105, compound

Product 1

HCID 57545330HCID 57545330, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

5-(Ethoxymethyl)-6-(2-methylpropyl)-8-(pyridin-3-ylmethoxy)-6H-imidazo[4,5-c]tetraazolo[1,5-a]quinoline (300 mg, 0.69 mmol) and triphenyphosphine (1 g, 4.17 mmol) were combined in a sealed vial and heated at 150° C. with stirring for 4 hours. The reaction was cooled to ambient temperature; diluted with chloroform; and purified by flash column chromatography on silica eluting with 5-10% gradient of methanol in chloroform. The clean fractions were concentrated under vacuum to provide a brown solid. This solid was refluxed for 1 hour in 4 mL of 3M aqueous HCl. The pH was adjusted to 14 by adding solid potassium hydroxide, and the resulting precipitate was filtered. The solid was dried under reduced pressure to provide 2-ethoxymethyl-1-(2-methylpropyl)-8-(pyridin-3-ylmethoxy)-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid, mp 204.0-206.0° C.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customand purified by flash column chromatography on silica eluting with 5-10% gradient of methanol in chloroform
  3. concentrationThe clean fractions were concentrated under vacuum
  4. customto provide a brown solid
  5. filtrationthe resulting precipitate was filtered
  6. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-3530b44e644c4d6f95d22941e01c58cb
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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