Bromoacetonitrile → HCID 22599677, compound

HRID 1759963Notes

Reaction equation

HRID 1759963 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.Br[CH2:20][C:21]#[N:22].[Cl-].[NH4+]>O1CCCC1>[Cl:3][C:4]1[CH:9]=[C:8]([N:10]([CH2:20][C:21]#[N:22])[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 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22599839HCID 22599839, compound

Product 1

HCID 22599677HCID 22599677, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 2 ml of tetrahydrofuran was suspended 0.07 g of sodium hydride (60% in oil), to which 0.6 ml of a tetrahydrofuran solution containing 0.3 g of 4-chloro-6-(2,3-difluoroanilino)pyrimidine was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes, to which 0.6 ml of a tetrahydrofuran solution containing 0.18 g of bromoacetonitrile was slowly added dropwise, 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 chloroform. The chloroform 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 0.24 g of 4-chloro-6-(N-cyanomethyl-N-(2,3-difluorophenyl)amino)pyrimidine.

Workup

  1. additionwas slowly added dropwise
  2. additionwas slowly added dropwise
  3. stirringby further stirring for 8 hours
  4. extractionextracted three times with chloroform
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22e2caef993c459aae5d10630db5b2a5
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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