Tributylphosphine → HCID 57597284, compound

HRID 1926003Notes

Reaction equation

HRID 1926003 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:18]3[N:25]([CH2:26][CH2:27]O)[CH:24]=[CH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1.C(P(CCCC)CCCC)CCC.N(/C(N1CCCCC1)=O)=N\C(N1CCCCC1)=O>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[CH:3]=[C:4]([N:16]2[C:17]3[C:18]4=[C:19]([CH:23]=[CH:24][N:25]4[CH2:26][CH2:27]2)[N:20]=[CH:21][N:22]=3)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 13831TributylphosphineHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 57597147HCID 57597147, compound

Product 1

HCID 57597284HCID 57597284, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 2-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethanol (50 mg) and tributylphosphine (54 mg) in toluene (2.5 mL) was added 1,1′-[(E)-diazene-1,2-diyldicarbonyl]dipiperidine (67 mg), and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was diluted with water (15 mL) and extracted with ethyl acetate (20 mL×3). The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (basic silica gel, eluent:ethyl acetate/methanol=100/0→90/10). The object fraction was concentrated under reduced pressure and dried to give the title compound (36 mg) as a white powder.

Workup

  1. extractionextracted with ethyl acetate (20 mL×3)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. concentrationThe object fraction was concentrated under reduced pressure
  6. customdried

Sources & evidence

ORD record
ord-f5a4c8e3a8c9460ba0b5bb6dafb0d551
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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