Ammonium Chloride → HCID 22599883, compound

HRID 1759861Notes

Reaction equation

HRID 1759861 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][C:16]#[N:17].Cl[C:19]1[CH:24]=[C:23]([O:25][CH2:26][C:27]#[C:28][CH3:29])[N:22]=[CH:21][N:20]=1.[Cl-].[NH4+]>O1CCCC1>[C:16]([CH:15]([C:19]1[CH:24]=[C:23]([O:25][CH2:26][C:27]#[C:28][CH3:29])[N:22]=[CH:21][N:20]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=1[F:7])#[N:17]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5189682,3-DifluorophenylacetonitrileHCID 121376024-(2-Butynyloxy)-6-chloropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 22599883HCID 22599883, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of tetrahydrofuran was suspended 0.41 g of potassium t-butoxide, to which 0.56 g of (2,3-difluorophenyl)acetonitrile and 0.5 g of 4-chloro-6-(2-butynyloxy)pyrimidine were added, followed by stirring at room temperature for 4 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 and washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 0.26 g of 4-(α-cyano-2,3-difluorobenzyl)-6-(2-butynyloxy)pyrimidine (the present compound (72)).

Workup

  1. extractionextracted three times with chloroform
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c724969af96b4181857d7b95404698cf
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

Loading…