3-formyl-4-hydroxybenzonitrile

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

Procedure: Prepared by the method of example 1 part (d) using 3-formyl-4-hydroxy-benzonitrile to give the title compound (1.4 g).

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: To n-butanol (100 ml.) add 5-cyano-salicylaldehyde (6 g.), 2-thiobarbituric acid (6 g.) and methanesulfonic acid (10 ml.) With stirring, heat the mixture to reflux for 11/2 hours. Cool, filter, and wash the solid with isopropanol and ether to yield 7-cyano-(1H,3H,5H)-(1)-benzopyrano-(2,3-d)-pyrimidine-4-one-2-thione. heat the mixture to reflux for 11/2 hours Cool filter wash the solid with isopropanol and ether

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

Procedure: Prepared by the method of example 1 part (d) using 3-formyl-4-hydroxy-benzonitrile to give the title compound (1.4 g).

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: Prepared by the method of example 1 part (d) using 3-formyl-4-hydroxy-benzonitrile to give the title compound (1.4 g).

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

Procedure: A solution of 5-cyano-2-hydroxybenzaldehyde (4.3 g) and (triphenylphosphoranylidene)acetaldehyde (9.4 g) in toluene (150 ml) was stirred at 70° C. for 2 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane/ethyl acetate=3/1 as an eluant to give the desired compound (2.3 g, yield 44%) as a colorless solid. The reaction mixture was concentrated in vacuo The residue was purified by chromatography on a silica gel column

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

Procedure: To a solution of 4-cyanophenol (25.0 g) in trifluoroacetic acid (150 ml) was added hexamethylenetetramine (50.0 g) and the mixture was stirred at 100° C. for 9 hours. After cooling to room temperature, sulfuric acid (50 ml) and water (300 ml) were added to the reaction mixture. The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with dichloromethane. The extract was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane/ethyl acetate=19/1 as an eluant to give the desired compound (4.3 g, yield 13%) as a colorless solid. After cooling to room temperature The resulting mixture was stirred at room temperature for 1 hour The reaction mixture was extracted with dichloromethane The extract was washed with water and brine The organic layer was dried over anhydrous magnesium sulfate filtered the filtrate concentrated in vacuo The residue was purified by chromatography on a silica gel column

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

Procedure: To n-butanol (100 ml.) add 5-cyano-salicylaldehyde (6 g.), 2-thiobarbituric acid (6 g.) and methanesulfonic acid (10 ml.) With stirring, heat the mixture to reflux for 11/2 hours. Cool, filter, and wash the solid with isopropanol and ether to yield 7-cyano-(1H,3H,5H)-(1)-benzopyrano-(2,3-d)-pyrimidine-4-one-2-thione. heat the mixture to reflux for 11/2 hours Cool filter wash the solid with isopropanol and ether