benzene-1,2-disulfonamide

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

Procedure: A mixture of 0.8 g of 2-amino-4,5,6-trimethylpyrimidine, 2.8 g of the crude sulfonyl isocyanate from Example 9 and a few crystals of DABCO in 25 ml of acetonitrile is stirred at room temperature for 16 hours. A small amount of unreacted aminopyrimidine is filtered off and the filtrate concentrated in-vacuo to give a hard glass. Crystallization from methanol gives N,N-diethyl-N'[4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide as a white solid. A small amount of unreacted aminopyrimidine is filtered off the filtrate concentrated in-vacuo to give a hard glass Crystallization from methanol

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

Procedure: A mixture of 0.8 g of 2-amino-4,5,6-trimethylpyrimidine, 2.8 g of the crude sulfonyl isocyanate from Example 9 and a few crystals of DABCO in 25 ml of acetonitrile is stirred at room temperature for 16 hours. A small amount of unreacted aminopyrimidine is filtered off and the filtrate concentrated in-vacuo to give a hard glass. Crystallization from methanol gives N,N-diethyl-N'[4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide as a white solid. A small amount of unreacted aminopyrimidine is filtered off the filtrate concentrated in-vacuo to give a hard glass Crystallization from methanol

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

Procedure: To a suspension of 0.7 g of 1,2-benzenedisulfonamide and 1.5 ml of trimethylaluminum in 70 ml of anhydrous methylene chloride was added 0.6 g of 4,6-dimethoxypyrimidin-2-ylcarbamic acid methyl ester under N2 with stirring. After addition, the mixture was stirred at room temperature for 30 minutes and was then heated to reflux for 12 hours. The reaction mixture was then cooled down to room temperature. To this mixture was added 50 ml of methylene chloride, 100 ml of water, 10 ml of acetic acid and 5 drops of concentrated hydrochloric acid. The mixture was then stirred at room temperature for 20 minutes and was filtered. The organic layer was then separated, washed with water, dried over sodium sulfate and concentrated. The residue was then chromatographed on silica gel (CH2Cl2 /acetic acid 1:1) to yield 0.2 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide, m.p. 192°-193° C. After addition the mixture was stirred at room temperature for 30 minutes was then heated to reflux for 12 hours The mixture was then stirred at room temperature for 20 minutes was filtered The organic layer was then separated washed with water dried over sodium sulfate concentrated The residue was then chromatographed on silica gel (CH2Cl2 /acetic acid 1:1)

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

Procedure: To a suspension of 0.7 g of 1,2-benzenedisulfonamide and 1.5 ml of trimethylaluminum in 70 ml of anhydrous methylene chloride was added 0.6 g of 4,6-dimethoxypyrimidin-2-ylcarbamic acid methyl ester under N2 with stirring. After addition, the mixture was stirred at room temperature for 30 minutes and was then heated to reflux for 12 hours. The reaction mixture was then cooled down to room temperature. To this mixture was added 50 ml of methylene chloride, 100 ml of water, 10 ml of acetic acid and 5 drops of concentrated hydrochloric acid. The mixture was then stirred at room temperature for 20 minutes and was filtered. The organic layer was then separated, washed with water, dried over sodium sulfate and concentrated. The residue was then chromatographed on silica gel (CH2Cl2 /acetic acid 1:1) to yield 0.2 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide, m.p. 192°-193° C. After addition the mixture was stirred at room temperature for 30 minutes was then heated to reflux for 12 hours The mixture was then stirred at room temperature for 20 minutes was filtered The organic layer was then separated washed with water dried over sodium sulfate concentrated The residue was then chromatographed on silica gel (CH2Cl2 /acetic acid 1:1)

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

Procedure: To a suspension of 0.7 g of 1,2-benzenedisulfonamide and 1.5 ml of trimethylaluminum in 70 ml of anhydrous methylene chloride was added 0.6 g of 4,6-dimethoxypyrimidin-2-ylcarbamic acid methyl ester under N2 with stirring. After addition, the mixture was stirred at room temperature for 30 minutes and was then heated to reflux for 12 hours. The reaction mixture was then cooled down to room temperature. To this mixture was added 50 ml of methylene chloride, 100 ml of water, 10 ml of acetic acid and 5 drops of concentrated hydrochloric acid. The mixture was then stirred at room temperature for 20 minutes and was filtered. The organic layer was then separated, washed with water, dried over sodium sulfate and concentrated. The residue was then chromatographed on silica gel (CH2Cl2 /acetic acid 1:1) to yield 0.2 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide, m.p. 192°-193° C. After addition the mixture was stirred at room temperature for 30 minutes was then heated to reflux for 12 hours The mixture was then stirred at room temperature for 20 minutes was filtered The organic layer was then separated washed with water dried over sodium sulfate concentrated The residue was then chromatographed on silica gel (CH2Cl2 /acetic acid 1:1)

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

Procedure: One gram of 1,2-benzenedisulfonylazide was added portionwise to 0.4 gm sodium borohydride in 15 ml of ethyl alcohol with stirring and cooling. After addition, the mixture was stirred with cooling (ice/acetone bath) for 2 hours and filtered. The solid was washed with cold ethyl alcohol and ether to yield 0.8 g of 1,2-benzenedisulfonamide, m.p. 250° C. Mass spec. (M/e) 236. cooling After addition the mixture was stirred filtered The solid was washed with cold ethyl alcohol and ether

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

Procedure: A mixture of 0.8 g of 2-amino-4,5,6-trimethylpyrimidine, 2.8 g of the crude sulfonyl isocyanate from Example 9 and a few crystals of DABCO in 25 ml of acetonitrile is stirred at room temperature for 16 hours. A small amount of unreacted aminopyrimidine is filtered off and the filtrate concentrated in-vacuo to give a hard glass. Crystallization from methanol gives N,N-diethyl-N'[4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide as a white solid. A small amount of unreacted aminopyrimidine is filtered off the filtrate concentrated in-vacuo to give a hard glass Crystallization from methanol