Iodoethane → HCID 22599861, compound

HRID 1592179Notes

Reaction equation

HRID 1592179 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([NH:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[CH2:21](I)[CH3:22].[H-].[Na+]>CN(C)C=O>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([N:12]([CH2:21][CH3:22])[CH2:13][C:14]([F:19])([F:20])[C:15]([F:16])([F:17])[F:18])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22599716HCID 22599716, compound

Product 1

HCID 22599861HCID 22599861, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 2 ml of N,N-dimethylformamide were dissolved 73 mg of 4-(2-butynyloxy)-6-(2,2,3,3,3-pentafluoropropylamino)pyrimidine and 47 mg of ethyl iodide, to which 12 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 3.5 hours. Then, ice water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed twice with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to preparative silica gel thin layer chromatography to give 43 mg of 4-(2-butynyloxy)-6-(N-ethyl-N-(2,2,3,3,3-pentafluoropropyl)amino)pyrimidine (the present compound (112)).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed twice with an aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-42f74019d6344914bfaad360d19710d7
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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