3-Pyridinemethanol → HCID 67229105, compound

HRID 598338Notes

Reaction equation

HRID 598338 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[N:10]3[N:18]=[N:19][N:20]=[C:9]3[C:8]=2[N:21]=1)[CH3:2].[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]O)[CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:32][C:28]4[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=4)[CH:15]=3)[N:10]3[N:18]=[N:19][N:20]=[C:9]3[C:8]=2[N:21]=1)[CH3:2]

Participants

6

Reactant 4

HCID 75103-Pyridinemethanol2×HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67227871HCID 67227871, compound

Product 1

HCID 67229105HCID 67229105, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(Ethoxymethyl)-6-(2-methylpropyl)-6H-imidazo[4,5-c]tetraazolo[1,5-α]quinolin-8-ol (260 mg, 0.76 mmol), was stirred in 10 mL of tetrahydrofuran (THF), 3-pyridylcarbinol (87 mg, 0.80 mmol), and triphenylphosphine (299 mg, 1.14 mmol). Diisopropyl azodicarboxylate (231 mg, 1.14 mmol) was added dropwise to the mixture. After 30 minutes, 2 additional drops of 3-pyridylcarbinol were added and the reaction was stirred overnight at ambient temperature. Analysis by thin layer chromatography indicated that a small amount of starting material still remained. Additional amounts of the reagents were added until all of the starting material was consumed. The reaction was filtered through an acidic ion exchange resin and the resin was washed with methanol, followed by 1M ammonia in methanol. The filtrate was concentrated under reduced pressure to provide 280 mg of 5-(ethoxymethyl)-6-(2-methylpropyl)-8-(pyridin-3-ylmethoxy)-6H-imidazo[4,5-c]tetraazolo[1,5-α]quinoline as an off white solid.

Workup

  1. additionAdditional amounts of the reagents were added until all of the starting material
  2. customwas consumed
  3. filtrationThe reaction was filtered through an acidic ion exchange resin
  4. washthe resin was washed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0867a155ec6f4de3beb38512634f3d09
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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