2-(2-sulfanylethyl)isoindole-1,3-dione

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

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

Procedure: A solution of 4-amino-2-chloromethylpyrimidine (11.6 g.) in methanol (20 ml.) was added over 15 minutes to a stirred mixture of sodium methoxide (4.32 g.), N-(2-mercaptoethyl)phthalimide (16.6 g.) and methanol (100 ml.), and the mixture stirred for 1 hour after the addition was complete and then evaporated to dryness. The residue was partitioned between 1N hydrochloric acid and ethyl acetate, and the aqueous phase separated and neutralised by the addition of sodium bicarbonate. The mixture was extracted with ethyl acetate and the extracts dried and evaporated to dryness, and the residue was recrystallised from acetonitrile to give 4-amino-2-[(2-phthalimidoethyl)thiomethyl)pyrimidine, m.p. 131°-133°. after the addition evaporated to dryness The residue was partitioned between 1N hydrochloric acid and ethyl acetate the aqueous phase separated neutralised by the addition of sodium bicarbonate The mixture was extracted with ethyl acetate the extracts dried evaporated to dryness the residue was recrystallised from acetonitrile

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

Procedure: A solution of 4-amino-2-chloromethylpyrimidine (11.6 g.) in methanol (20 ml.) was added over 15 minutes to a stirred mixture of sodium methoxide (4.32 g.), N-(2-mercaptoethyl)phthalimide (16.6 g.) and methanol (100 ml.), and the mixture stirred for 1 hour after the addition was complete and then evaporated to dryness. The residue was partitioned between 1N hydrochloric acid and ethyl acetate, and the aqueous phase separated and neutralised by the addition of sodium bicarbonate. The mixture was extracted with ethyl acetate and the extracts dried and evaporated to dryness, and the residue was recrystallised from acetonitrile to give 4-amino-2-[(2-phthalimidoethyl)thiomethyl)pyrimidine, m.p. 131°-133°. after the addition evaporated to dryness The residue was partitioned between 1N hydrochloric acid and ethyl acetate the aqueous phase separated neutralised by the addition of sodium bicarbonate The mixture was extracted with ethyl acetate the extracts dried evaporated to dryness the residue was recrystallised from acetonitrile

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

Procedure: 80% Sodium hydride (0.155 g) was added portionwise to a solution of 2-phthalimido-ethanethiol (1.03 g) in dry dimethylformamide at 0°. After 20 mins a solution of 2-furanethanol, 4-methylbenzenesulphonate (1.33 g) in dry dimethylformamide was added dropwise and the solution stirred overnight at room temperature. The mixture was poured into ice-water and 2-[[2-furanyl)ethyl]thio]ethyl-1H-isoindole-1,3(2H)-dione isolated as a white solid (1.3 g) m.p. 53°-55°.

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

Procedure: A solution of 4-amino-2-chloromethylpyrimidine (11.6 g.) in methanol (20 ml.) was added over 15 minutes to a stirred mixture of sodium methoxide (4.32 g.), N-(2-mercaptoethyl)phthalimide (16.6 g.) and methanol (100 ml.), and the mixture stirred for 1 hour after the addition was complete and then evaporated to dryness. The residue was partitioned between 1N hydrochloric acid and ethyl acetate, and the aqueous phase separated and neutralised by the addition of sodium bicarbonate. The mixture was extracted with ethyl acetate and the extracts dried and evaporated to dryness, and the residue was recrystallised from acetonitrile to give 4-amino-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine, m.p. 131°-133°. after the addition evaporated to dryness The residue was partitioned between 1N hydrochloric acid and ethyl acetate the aqueous phase separated neutralised by the addition of sodium bicarbonate The mixture was extracted with ethyl acetate the extracts dried evaporated to dryness the residue was recrystallised from acetonitrile

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

Procedure: 80% Sodium hydride (0.155 g) was added portionwise to a solution of 2-phthalimido-ethanethiol (1.03 g) in dry dimethylformamide at 0°. After 20 mins a solution of 2-furanethanol, 4-methylbenzenesulphonate (1.33 g) in dry dimethylformamide was added dropwise and the solution stirred overnight at room temperature. The mixture was poured into ice-water and 2-[[2-furanyl)ethyl]thio]ethyl-1H-isoindole-1,3(2H)-dione isolated as a white solid (1.3 g) m.p. 53°-55°.

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

Procedure: A solution of 4-amino-2-chloromethylpyrimidine (11.6 g.) in methanol (20 ml.) was added over 15 minutes to a stirred mixture of sodium methoxide (4.32 g.), N-(2-mercaptoethyl)phthalimide (16.6 g.) and methanol (100 ml.), and the mixture stirred for 1 hour after the addition was complete and then evaporated to dryness. The residue was partitioned between 1N hydrochloric acid and ethyl acetate, and the aqueous phase separated and neutralised by the addition of sodium bicarbonate. The mixture was extracted with ethyl acetate and the extracts dried and evaporated to dryness, and the residue was recrystallised from acetonitrile to give 4-amino-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine, m.p. 131°-133°. after the addition evaporated to dryness The residue was partitioned between 1N hydrochloric acid and ethyl acetate the aqueous phase separated neutralised by the addition of sodium bicarbonate The mixture was extracted with ethyl acetate the extracts dried evaporated to dryness the residue was recrystallised from acetonitrile

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

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

Procedure: A solution of 4-amino-2-chloromethylpyrimidine (11.6 g.) in methanol (20 ml.) was added over 15 minutes to a stirred mixture of sodium methoxide (4.32 g.), N-(2-mercaptoethyl)phthalimide (16.6 g.) and methanol (100 ml.), and the mixture stirred for 1 hour after the addition was complete and then evaporated to dryness. The residue was partitioned between 1 N hydrochloric acid and ethyl acetate, and the aqueous phase separated and neutralised by the addition of sodium bicarbonate. The mixture was extracted with ethyl acetate and the extracts dried and evaporated to dryness, and the residue was recrystallised from acetonitrile to give 4-amino-2-[(2-phthalimidoethyl)thiomethyl)pyrimidine, m.p. 131°-133°. after the addition evaporated to dryness The residue was partitioned between 1 N hydrochloric acid and ethyl acetate the aqueous phase separated neutralised by the addition of sodium bicarbonate The mixture was extracted with ethyl acetate the extracts dried evaporated to dryness the residue was recrystallised from acetonitrile

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

Procedure: To a solution of N-(2-mercaptoethyl) phthalimide (28.8 g, 0.139 mol) in dry methanol (250 ml) is added sodium methoxide (7.5 g, 0.139 mol) with cooling and stirring. This mercaptide solution is added to 2,6-bis(chloromethyl)pyridine (24.5 g, 0.139 mol) in dry methanol (250 ml). The mixture is stirred at room temperature for 21/2 hours and is filtered to remove the precipitated solid. Then dimethylamine (6.9 g, 0.153 mol) in cold methanol (150 ml) is added to the filtrate and the mixture is stirred at room temperature overnight. The solvent is removed in vacuo leaving an amber gum. The gum is taken up in methylene chloride (200 ml) and is washed with aqueous sodium bicarbonate and with water. The methylene chloride layer is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. This gives 24.3 g of 6-dimethylaminomethyl-2-[(2-phthalimidoethyl)thiomethyl]pyridine as a crude amber gum. with cooling The mixture is stirred at room temperature for 21/2 hours is filtered to remove the precipitated solid the mixture is stirred at room temperature overnight The solvent is removed in vacuo leaving an amber gum is washed with aqueous sodium bicarbonate and with water The methylene chloride layer is dried over anhydrous sodium sulfate filtered concentrated in vacuo

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

Procedure: A solution of 4-amino-2-chloromethylpyrimidine (11.6 g.) in methanol (20 ml.) was added over 15 minutes to a stirred mixture of sodium methoxide (4.32 g.), N-(2-mercaptoethyl)phthalimide (16.6 g.) and methanol (100 ml.), and the mixture stirred for 1 hour after the addition was complete and then evaporated to dryness. The residue was partitioned between 1N hydrochloric acid and ethyl acetate, and the aqueous phase separated and neutralised by the addition of sodium bicarbonate. The mixture was extracted with ethyl acetate and the extracts dried and evaporated to dryness, and the residue was recrystallised from acetonitrile to give 4-amino-2-[(2-phthalimidoethyl)thiomethyl)pyrimidine, m.p. 131°-133°. after the addition evaporated to dryness The residue was partitioned between 1N hydrochloric acid and ethyl acetate the aqueous phase separated neutralised by the addition of sodium bicarbonate The mixture was extracted with ethyl acetate the extracts dried evaporated to dryness the residue was recrystallised from acetonitrile

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

Procedure: 80% Sodium hydride (0.155 g) was added portionwise to a solution of 2-phthalimido-ethanethiol (1.03 g) in dry dimethylformamide at 0°. After 20 mins a solution of 2-furanethanol, 4-methylbenzenesulphonate (1.33 g) in dry dimethylformamide was added dropwise and the solution stirred overnight at room temperature. The mixture was poured into ice-water and 2-[[2-furanyl)ethyl]thio]ethyl-1H-isoindole-1,3(2H)-dione isolated as a white solid (1.3 g) m.p. 53°-55°.