Ammonium Chloride → HCID 22599829, compound

HRID 1759872Notes

Reaction equation

HRID 1759872 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[CH2:10][C:11]#[N:12].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:11]([CH:10]([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[C:13]([F:17])=[CH:14][CH:15]=[CH:16][C:8]=1[Cl:7])#[N:12]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1235752-Chloro-6-fluorophenylacetonitrileHCID 121376024-(2-Butynyloxy)-6-chloropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 22599829HCID 22599829, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of tetrahydrofuran was suspended 0.46 g of potassium t-butoxide, to which 0.56 g of 2-chloro-6-fluorobenzylcyanide of formula and 0.5 g of 4-chloro-6-(2-butynyloxy)pyrimidine were added, followed by stirring at room temperature 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 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 0.25 g of 4-(α-cyano-2-chloro-6-fluorobenzyl)-6-(2-butynyloxy)pyrimidine (the present compound (84)).

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-134b6aac8e0c4e8ca6bd4e554fb9148f
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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