4-methylsulfanylbutan-1-ol

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

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

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

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

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

Procedure: 4-(Isopropylamino)-6-methoxyquinazolin-7-ol (380 mg, 1.63 mmol) is dissolved in methylene chloride (10 ml) under an argon atmosphere, treated with triphenylphosphine (641 mg, 2.44 mmol), azodicarboxylic acid dipiperidide (617 mg, 2.44 mmol) and 4-(methylthio)butan-1-ol (235 mg, 1.96 mmol) and stirred at room temperature for 20 hours. The batch is diluted with methylene chloride and water, and the organic phase is separated off and concentrated. The desired product is obtained after chromatography by means of preparative HPLC in 43% yield (258 mg). the organic phase is separated off concentrated

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

Procedure: 4-(Isopropylamino)-6-methoxyquinazolin-7-ol (380 mg, 1.63 mmol) is dissolved in methylene chloride (10 ml) under an argon atmosphere, treated with triphenylphosphine (641 mg, 2.44 mmol), azodicarboxylic acid dipiperidide (617 mg, 2.44 mmol) and 4-(methylthio)butan-1-ol (235 mg, 1.96 mmol) and stirred at room temperature for 20 hours. The batch is diluted with methylene chloride and water, and the organic phase is separated off and concentrated. The desired product is obtained after chromatography by means of preparative HPLC in 43% yield (258 mg). the organic phase is separated off concentrated

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

Procedure: The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (0.94 g, 3.1 mmol) obtained in Example 5 was dissolved in toluene (15 ml). After addition of 4-(methylthio)-1-butanol (0.25 ml, 2.1 mmol) and cyanomethylenetri-n-butylphosphorane (1.0 g, 4.1 mmol), the resulting mixture was heated under reflux for 14 hours under an argon atmosphere. The reaction mixture was allowed to cool down. Then, 4-(methylthio)-1-butanol (0.25 ml, 2.1 mmol) was added, followed by heating under reflux for 6 hours under an argon atmosphere. The reaction mixture was allowed to cool down and then, concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to yield a colorless oil. The resulting colorless oil was solidified with hexane, whereby the title compound (0.55 g, 44%) was obtained as a white powder. the resulting mixture was heated under reflux for 14 hours under an argon atmosphere to cool down by heating under reflux for 6 hours under an argon atmosphere to cool down concentrated under reduced pressure The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to yield a colorless oil

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

Procedure: Prepared as in Example 215c from 4-(methylthio)butan-1-ol and 2,6-dinitrobenzonitrile in 89% yield. MS 267 (MH+).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(Methylthio)butan-1-ol (721 mg, 6.0 mmol) was dissolved in methanol (15 mL) and cooled to 0° C. in an ice bath. 2KHSO5.KHSO4.K2SO4 (4057 mg, 6.60 mmol), dissolved in water (15 mL), was added dropwise over a 10 minute period. Upon completion of addition, the reaction mixture was removed from the ice bath and warmed to room temperature and stirred for one hour. The reaction mixture was diluted with water (15 mL) and extracted with ethyl acetate (50 mL). The aqueous layer was concentrated to dryness, and the residue was diluted with dichloromethane, stirred 30 minutes and filtered. The filtrate was concentrated to give the title compound as a clear oil (825 mg, 90%). was added dropwise over a 10 minute period Upon completion of addition the reaction mixture was removed from the ice bath warmed to room temperature The reaction mixture was diluted with water (15 mL) extracted with ethyl acetate (50 mL) The aqueous layer was concentrated to dryness the residue was diluted with dichloromethane stirred 30 minutes filtered The filtrate was concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(Methylthio)butan-1-ol (721 mg, 6.0 mmol) was dissolved in methanol (15 mL) and cooled to 0° C. in an ice bath. 2KHSO5.KHSO4.K2SO4 (4057 mg, 6.60 mmol), dissolved in water (15 mL), was added dropwise over a 10 minute period. Upon completion of addition, the reaction mixture was removed from the ice bath and warmed to room temperature and stirred for one hour. The reaction mixture was diluted with water (15 mL) and extracted with ethyl acetate (50 mL). The aqueous layer was concentrated to dryness, and the residue was diluted with dichloromethane, stirred 30 minutes and filtered. The filtrate was concentrated to give the title compound as a clear oil (825 mg, 90%). was added dropwise over a 10 minute period Upon completion of addition the reaction mixture was removed from the ice bath warmed to room temperature The reaction mixture was diluted with water (15 mL) extracted with ethyl acetate (50 mL) The aqueous layer was concentrated to dryness the residue was diluted with dichloromethane stirred 30 minutes filtered The filtrate was concentrated

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

Procedure: Prepared as in Example 215c from 4-(methylthio)butan-1-ol and 2,6-dinitrobenzonitrile in 89% yield. MS 267 (MH+).

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

Procedure: Prepared as in Example 215c from 4-(methylthio)butan-1-ol and 2,6-dinitrobenzonitrile in 89% yield. MS 267 (MH+).