[4-(2-chloroethyl)phenyl]methanol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To 200 mg (0.99 mmol) 5-benzyloxy-2H-pyridazin-3-one (preparation 5) in 1.0 mL DMF is added 645 mg (1.98 mmol) cesium carbonate and the mixture is stirred 15 min at RT. Then 518 mg (1.98 mmol) [4-(2-iodo-ethyl)-phenyl]-methanol (preparation 1b) is added and the reaction mixture is stirred overnight. The mixture is diluted with EtOAc, a few drops of MeOH and water. The layers are separated, the organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. The precipitate is elutriated in acetone and the product is collected by filtration and dried. the reaction mixture is stirred overnight The layers are separated the organic phase is washed with water dried over MgSO4 filtered the solvent is evaporated the product is collected by filtration dried

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3.00 g (14.8 mmol) 6-benzyloxy-3H-pyrimidin-4-one in 15 mL DMF is added 2.66 g (15.6 mmol) [4-(2-chloro-ethyl)-phenyl]-methanol (preparation 1b) and 5.13 g (37.1 mmol) potassium carbonate. The reaction mixture is stirred 3 h at 100° C., filtered and the solvent is evaporated. The residue is put on silica gel and is purified by chromatography (silica gel; PE/EtOAc 1:1 to 2.5:7.5) filtered the solvent is evaporated is purified by chromatography (silica gel; PE/EtOAc 1:1 to 2.5:7.5)

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

Procedure: To 60.0 g (352 mmol) [4-(2-chloro-ethyl)-phenyl]-MeOH (preparation 1a) in 280 mL of acetone is added 105 g (703 mmol) sodium iodide. The reaction mixture is refluxed overnight and cooled to RT. After filtration, the residue is elutriated in DCM, filtered and dried. The reaction mixture is refluxed overnight After filtration filtered dried

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 100 g (525 mmol) 4-(2-chloro-ethyl)-benzoic acid in 1.0 L of THF is added 170 g (1050 mmol) CDI in small portions. The mixture is stirred at 60° C. until the gas evolution ceased. After cooling to RT, the mixture is slowly added into a solution of 39.7 g (1050 mmol) sodium borohydride in ice water and is stirred for 3 h at RT. The solution is acidified with diluted HCL and extracted twice with EtOAc. The organic phase is separated and dried over MgSO4. After evaporation of the solvent, the residue is dissolved in water/EtOAc. The aqueous phase is separated, washed once with EtOAc and the combined organic phase is dried over MgSO4. After evaporation of the solvent the residue is purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent. After cooling to RT is stirred for 3 h at RT extracted twice with EtOAc The organic phase is separated dried over MgSO4 After evaporation of the solvent the residue is dissolved in water/EtOAc The aqueous phase is separated washed once with EtOAc the combined organic phase is dried over MgSO4 After evaporation of the solvent the residue is purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 100 g (525 mmol) 4-(2-chloro-ethyl)-benzoic acid in 1.0 L of THF is added 170 g (1050 mmol) CDI in small portions. The mixture is stirred at 60° C. until the gas evolution ceased. After cooling to RT, the mixture is slowly added into a solution of 39.7 g (1050 mmol) sodium borohydride in ice water and is stirred for 3 h at RT. The solution is acidified with diluted HCL and extracted twice with EtOAc. The organic phase is separated and dried over MgSO4. After evaporation of the solvent, the residue is dissolved in water/EtOAc. The aqueous phase is separated, washed once with EtOAc and the combined organic phase is dried over MgSO4. After evaporation of the solvent the residue is purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent. After cooling to RT is stirred for 3 h at RT extracted twice with EtOAc The organic phase is separated dried over MgSO4 After evaporation of the solvent the residue is dissolved in water/EtOAc The aqueous phase is separated washed once with EtOAc the combined organic phase is dried over MgSO4 After evaporation of the solvent the residue is purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To 200 mg (0.99 mmol) 5-benzyloxy-2H-pyridazin-3-one (preparation 5) in 1.0 mL DMF is added 645 mg (1.98 mmol) cesium carbonate and the mixture is stirred 15 min at RT. Then 518 mg (1.98 mmol) [4-(2-iodo-ethyl)-phenyl]-methanol (preparation 1b) is added and the reaction mixture is stirred overnight. The mixture is diluted with EtOAc, a few drops of MeOH and water. The layers are separated, the organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. The precipitate is elutriated in acetone and the product is collected by filtration and dried. the reaction mixture is stirred overnight The layers are separated the organic phase is washed with water dried over MgSO4 filtered the solvent is evaporated the product is collected by filtration dried

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3.00 g (14.8 mmol) 6-benzyloxy-3H-pyrimidin-4-one in 15 mL DMF is added 2.66 g (15.6 mmol) [4-(2-chloro-ethyl)-phenyl]-methanol (preparation 1b) and 5.13 g (37.1 mmol) potassium carbonate. The reaction mixture is stirred 3 h at 100° C., filtered and the solvent is evaporated. The residue is put on silica gel and is purified by chromatography (silica gel; PE/EtOAc 1:1 to 2.5:7.5) filtered the solvent is evaporated is purified by chromatography (silica gel; PE/EtOAc 1:1 to 2.5:7.5)

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

Procedure: To 60.0 g (352 mmol) [4-(2-chloro-ethyl)-phenyl]-MeOH (preparation 1a) in 280 mL of acetone is added 105 g (703 mmol) sodium iodide. The reaction mixture is refluxed overnight and cooled to RT. After filtration, the residue is elutriated in DCM, filtered and dried. The reaction mixture is refluxed overnight After filtration filtered dried

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 100 g (525 mmol) 4-(2-chloro-ethyl)-benzoic acid in 1.0 L of THF is added 170 g (1050 mmol) CDI in small portions. The mixture is stirred at 60° C. until the gas evolution ceased. After cooling to RT, the mixture is slowly added into a solution of 39.7 g (1050 mmol) sodium borohydride in ice water and is stirred for 3 h at RT. The solution is acidified with diluted HCL and extracted twice with EtOAc. The organic phase is separated and dried over MgSO4. After evaporation of the solvent, the residue is dissolved in water/EtOAc. The aqueous phase is separated, washed once with EtOAc and the combined organic phase is dried over MgSO4. After evaporation of the solvent the residue is purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent. After cooling to RT is stirred for 3 h at RT extracted twice with EtOAc The organic phase is separated dried over MgSO4 After evaporation of the solvent the residue is dissolved in water/EtOAc The aqueous phase is separated washed once with EtOAc the combined organic phase is dried over MgSO4 After evaporation of the solvent the residue is purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent