2-methylsulfanyl-1,4,5,6-tetrahydropyrimidine;hydroiodide

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

Procedure: Procedure 1 is repeated with substitution of 2-(methylthio)-3,4,5,6-tetrahydropyrimidine hydroiodide for the 2-(methylthio)-2-imidazoline hydroiodide specified. The resulting 8-amino-3,4-dihydro-9-[(4-chlorophenyl)methyl]-7-nitroso-2H,5H-pyrimido(1,2-a)pyrimidin-6(9H)-one is converted to the corresponding 7-formylamino compound according to the method of Procedure 2, and the latter is then cyclized to the desired product by the method of Procedure 4.

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

Procedure: A flask containing a mixture of 2,2-diphenylethylamine (5.92 g; 3.00×10-2 mole) and 2-methylthio-1,4,5,6-tetrahydropyrimidine hydroiodide (7.74 g, 3.00×10-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 150°-168° C. for 1.5 hours. The resulting yellow glass was dissolved in methanol. The methanol was evaporated and the resulting yellow oil was dissolved in dichloromethane. This solution was transferred to a separatory funnel where it was washed with 2N aqueous NaOH and saturated aqueous NaCl. After drying over anhydrous Na2SO4, the dichloromethane was evaporated giving a foam which was dissolved in methanol (125 ml). This solution was cooled to 0° C. at which time it was treated with a methanolic solution of HCl. After 10-15 minutes most of the methanol was evaporated and 2-butanone was added. After several days the crystals were collected by filtration. Recrystallization from isopropanol afforded 2-(2,2-diphenylethylamino)-1,4,5,6-tetrahydropyrimidine hydrochloride as off-white crystals: 3.80 g (40%), m.p. 180°-182° C. A flask containing was immersed in an oil bath had been preheated to ca. 155° C The methanol was evaporated the resulting yellow oil was dissolved in dichloromethane This solution was transferred to a separatory funnel where it was washed with 2N aqueous NaOH and saturated aqueous NaCl After drying over anhydrous Na2SO4 the dichloromethane was evaporated giving a foam which After 10-15 minutes most of the methanol was evaporated 2-butanone was added After several days the crystals were collected by filtration Recrystallization from isopropanol

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

Procedure: A flask containing a mixture of 2,2-diphenylethylamine (5.92 g; 3.00×10-2 mole) and 2-methylthio-1,4,5,6-tetrahydropyrimidine hydroiodide (7.74 g, 3.00×10-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 150°-168° C. for 1.5 hours. The resulting yellow glass was dissolved in methanol. The methanol was evaporated and the resulting yellow oil was dissolved in dichloromethane. This solution was transferred to a separatory funnel where it was washed with 2N aqueous NaOH and saturated aqueous NaCl. After drying over anhydrous Na2SO4, the dichloromethane was evaporated giving a foam which was dissolved in methanol (125 ml). This solution was cooled to 0° C. at which time it was treated with a methanolic solution of HCl. After 10-15 minutes most of the methanol was evaporated and 2-butanone was added. After several days the crystals were collected by filtration. Recrystallization from isopropanol afforded 2-(2,2-diphenylethylamino)-1,4,5,6-tetrahydropyrimidine hydrochloride as off-white crystals: 3.80 g (40%), m.p. 180°-182° C. A flask containing was immersed in an oil bath had been preheated to ca. 155° C The methanol was evaporated the resulting yellow oil was dissolved in dichloromethane This solution was transferred to a separatory funnel where it was washed with 2N aqueous NaOH and saturated aqueous NaCl After drying over anhydrous Na2SO4 the dichloromethane was evaporated giving a foam which After 10-15 minutes most of the methanol was evaporated 2-butanone was added After several days the crystals were collected by filtration Recrystallization from isopropanol

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

Procedure: Procedure 1 is repeated with substitution of 2-(methylthio)-3,4,5,6-tetrahydropyrimidine hydroiodide for the 2-(methylthio)-2-imidazoline hydroiodide specified. The resulting 8-amino-3,4-dihydro-9-[(4-chlorophenyl)methyl]-7-nitroso-2H,5H-pyrimido(1,2-a)pyrimidin-6(9H)-one is converted to the corresponding 7-formylamino compound according to the method of Procedure 2, and the latter is then cyclized to the desired product by the method of Procedure 4.

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

Procedure: - Procedure 1 is repeated with substitution of 2-(methylthio)-3,4,5,6-tetrahydropyrimidine hydroiodide for the 2-(methylthio)-2-imidazoline hydroiodide specified. The resulting 8-amino-3,4-dihydro-9-[(4-chlorophenyl)methyl]-7-nitroso-2H,5H-pyrimido(1,2-a)pyrimidin-6(9H)-one is converted to the corresponding 7-formylamino compound to the method of Procedure 2, and the latter is then cyclized to the desired product by the method of Procedure 4.

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

Procedure: Procedure 1 is repeated with substitution of 2-(methylthio)-3,4,5,6-tetrahydropyrimidine hydroiodide for the 2-(methylthio)-2-imidazoline hydroiodide specified. The resulting 8-amino-3,4-dihydro-9-[(4-chlorophenyl)methyl]-7-nitroso-2H,5H-pyrimido(1,2-a)pyrimidin-6(9H)-one is converted to the corresponding 7-formylamino compound according to the method of Procedure 2, and the latter is then cyclized to the desired product by the method of Procedure 4.

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

Procedure: --Procedure 1 is repeated with substitution of 2-(methylthio)-3,4,5,6-tetrahydropyrimidine hydroiodide for the 2-(methylthio)-2-imidazoline hydroiodide specified. The resulting 8-amino-3,4-dihydro-9-[(4-chlorophenyl)methyl]-7-nitroso-2H,5H-pyrimido(1,2-a)pyrimidin-6(9H)-one is converted to the corresponding 7-formylamino compound according to the method of Procedure 2, and the latter is then cyclized to the desired product by the method of Procedure 4.

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

Procedure: Procedure 1 is repeated with substitution of 2-(methylthio)-3,4,5,6-tetrahydropyrimidine hydroiodide for the 2-(methylthio)-2-imidazoline hydroiodide specified. The resulting 8-amino-3,4-dihydro-9-[(4-chlorophenyl)methyl]-7-nitroso-2H,5H-pyrimido(1,2-a) pyrimidin-6(9H)-one is converted to the corresponding 7-formylamino compound according to the method of Procedure 2, and the latter is then cyclized to the desired product by the method of Procedure 4.

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

Procedure: A flask containing a mixture of 2,2-diphenylethylamine (5.92 g; 3.00×10-2 mole) and 2-methylthio-1,4,5,6-tetrahydropyrimidine hydroiodide (7.74 g, 3.00×10-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 150°-168° C. for 1.5 hours. The resulting yellow glass was dissolved in methanol. The methanol was evaporated and the resulting yellow oil was dissolved in dichloromethane. This solution was transferred to a separatory funnel where it was washed with 2N aqueous NaOH and saturated aqueous NaCl. After drying over anhydrous Na2SO4, the dichloromethane was evaporated giving a foam which was dissolved in methanol (125 ml). This solution was cooled to 0° C. at which time it was treated with a methanolic solution of HCl. After 10-15 minutes most of the methanol was evaporated and 2-butanone was added. After several days the crystals were collected by filtration. Recrystallization from isopropanol afforded 2-(2,2-diphenylethylamino)-1,4,5,6-tetrahydropyrimidine hydrochloride as off-white crystals: 3.80 g (40%), m.p. 180°-182° C. A flask containing was immersed in an oil bath had been preheated to ca. 155° C The methanol was evaporated the resulting yellow oil was dissolved in dichloromethane This solution was transferred to a separatory funnel where it was washed with 2N aqueous NaOH and saturated aqueous NaCl After drying over anhydrous Na2SO4 the dichloromethane was evaporated giving a foam which After 10-15 minutes most of the methanol was evaporated 2-butanone was added After several days the crystals were collected by filtration Recrystallization from isopropanol

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

Procedure: Procedure 1 is repeated with substitution of 2-(methylthio)-3,4,5,6-tetrahydropyrimidine hydroiodide for the 2-(methylthio)-2-imidazoline hydroiodide specified. The resulting 8-amino-3,4-dihydro-9-[(4-chlorophenyl)methyl]-7-nitroso-2H,5H-pyrimido(1,2-a)pyrimidin-6(9H)-one is converted to the corresponding 7-formylamino compound according to the method of Procedure 2, and the latter is then cyclized to the desired product by the method of Procedure 4.