Iodoethane → HCID 22599879, compound

HRID 1759904Notes

Reaction equation

HRID 1759904 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([NH:12][CH2:13][C:14]([F:17])([F:16])[F:15])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[CH2:18](I)[CH3:19].[H-].[Na+].O1CCCC1>CN(C)C=O>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([N:12]([CH2:18][CH3:19])[CH2:13][C:14]([F:16])([F:17])[F:15])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 22599819HCID 22599819, compound

Product 1

HCID 22599879HCID 22599879, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 2 ml of N,N-dimethylformamide were dissolved 40 mg of 4-(2-butynyloxy)-6-(2,2,2-trifluoroethylamino)pyrimidine and 31 mg of ethyl iodide, to which 8 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 1 hour. Then, 6 ml of tetrahydrofuran was added, and the mixture was further stirred at room temperature for 4.5 hours. Then, ice water was added to the reaction mixture, from which the tetrahydrofuran was distilled out under reduced pressure. The residue was extracted with tert-butyl methyl ether. 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 silica gel thin layer chromatography to give 37 mg of 4-(2-butynyloxy)-6-(N-ethyl-N-2,2,2-trifluoroethylamino)pyrimidine (the present compound (115)).

Workup

  1. stirringthe mixture was further stirred at room temperature for 4.5 hours
  2. distillationwas distilled out under reduced pressure
  3. extractionThe residue was extracted with tert-butyl methyl ether
  4. washThe organic layer was washed twice with an aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0680ae20435d40f9afff6a1c6dd67a53
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

Loading…