Iodoethane → HCID 22599795, compound

HRID 1759992Notes

Reaction equation

HRID 1759992 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:7]=[CH:6][N:5]=1.I[CH2:20][CH3:21].[Cl-].[NH4+]>O1CCCC1>[Cl:3][C:4]1[CH:9]=[C:8]([N:10]([CH2:20][CH3:21])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22599839HCID 22599839, compound

Product 1

HCID 22599795HCID 22599795, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 4.2 ml of tetrahydrofuran was suspended 0.12 g of sodium hydride (60% in oil), to which 0.8 ml of a tetrahydrofuran solution containing 0.5 g of 4-chloro-6-(2,3-difluorophenylamino)pyrimidine was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes, to which 0.8 ml of a tetrahydrofuran solution containing 0.48 g of iodoethane was slowly added dropwise at 0° C., followed by further stirring for 8 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with t-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.23 g of 4-chloro-6-(N-ethyl-N-(2,3-difluorophenyl)amino)pyrimidine.

Workup

  1. additionwas slowly added dropwise
  2. additionwas slowly added dropwise at 0° C.
  3. stirringby further stirring for 8 hours
  4. extractionextracted three times with t-butyl methyl ether
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d52864f10c9e4454871670cdaddd6c4f
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

Loading…