Ethyl Acetate → HCID 90051763, compound

HRID 2284734Notes

Reaction equation

HRID 2284734 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[C:8]([NH:22][CH2:23][CH2:24][CH3:25])=[N:9][C:10]([NH:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)=[N:11][CH:12]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[O:1]=[CH:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[C:8]([NH:22][CH2:23][CH2:24][CH3:25])=[N:9][C:10]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]#[N:19])=[CH:20][CH:21]=2)=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 90051762HCID 90051762, compound

Product 1

HCID 90051763HCID 90051763, compoundYield 243.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((5-(5-hydroxy-1-pentyn-1-yl)-4-(propylamino)pyrimidin-2-yl)amino)benzonitrile (G11, 124 mg) in methylene chloride (4 mL), 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H)-one (313 mg) was added at room temperature, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, ethyl acetate and 10% aqueous sodium thiosulfate were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 4-((5-(5-oxo-1-pentyn-1-yl)-4-(propylamino)pyrimidin-2-yl)amino)benzonitrile (G12, 300 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a5037f8a23b64ab6b9368c82fa4777c4
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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