2-(2-chloro-6-fluorophenyl)acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-Chloro-6-fluoro-benzyl)-4,5-dihydro-1H-imidazole was prepared from (2-chloro-6-fluoro-phenyl)-acetonitrile and ethylene diamine in analogy to Example 22; isolated as hydrochloride: colourless powder; MS (ISP): 212.9 ((M+H)+.).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-Chloro-6-fluoro-benzyl)-4,5-dihydro-1H-imidazole was prepared from (2-chloro-6-fluoro-phenyl)-acetonitrile and ethylene diamine in analogy to Example 22; isolated as hydrochloride: colourless powder; MS (ISP): 212.9 ((M+H)+.).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-Chloro-6-fluoro-benzyl)-4,5-dihydro-1H-imidazole was prepared from (2-chloro-6-fluoro-phenyl)-acetonitrile and ethylene diamine in analogy to Example 22; isolated as hydrochloride: colourless powder; MS (ISP): 212.9 ((M+H)+.).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10.0 g (59 mmol) of (2-chloro-6-fluorophenyl)acetonitrile in 50 ml of ethanol were admixed with 7.0 g (101 mmol) of hydroxylamine hydrochloride and then with 7.5 g (71 mmol) of sodium carbonate dissolved in 30 ml of water. This mixture was refluxed for 4 h, poured into aqueous sodium dihydrogen phosphate buffer (pH 7.8) and extracted with methylene chloride, and the extract was dried over sodium sulfate. The solvent was removed under reduced pressure, and 4.9 g of product were obtained from the extract. A further 3.7 g precipitated from the aqueous phase. Overall yield: 8.6 g, which were directly reacted further. This mixture was refluxed for 4 h extracted with methylene chloride the extract was dried over sodium sulfate The solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10.0 g (59 mmol) of (2-chloro-6-fluorophenyl)acetonitrile in 50 ml of ethanol were admixed with 7.0 g (101 mmol) of hydroxylamine hydrochloride and then with 7.5 g (71 mmol) of sodium carbonate dissolved in 30 ml of water. This mixture was refluxed for 4 h, poured into aqueous sodium dihydrogen phosphate buffer (pH 7.8) and extracted with methylene chloride, and the extract was dried over sodium sulfate. The solvent was removed under reduced pressure, and 4.9 g of product were obtained from the extract. A further 3.7 g precipitated from the aqueous phase. Overall yield: 8.6 g, which were directly reacted further. This mixture was refluxed for 4 h extracted with methylene chloride the extract was dried over sodium sulfate The solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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)). extracted three times with chloroform washed with a saturated aqueous sodium chloride solution The organic layer was dried over anhydrous magnesium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-Chloro-6-fluoro-benzyl)-4,5-dihydro-1H-imidazole was prepared from (2-chloro-6-fluoro-phenyl)-acetonitrile and ethylene diamine in analogy to Example 22; isolated as hydrochloride: colourless powder; MS (ISP): 212.9 ((M+H)+.).