propylurea

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

Procedure: This method was utilized to prepare the N-3 propylpurines. The starting material used was n-propyl urea condensed with ethyl cyanoacetate in the presence of sodium ethoxide to yield the 6-amino-1-propylpyrimidinedione in moderate yield. Commercially available 3-n-propylxanthine could also be used as the starting material.

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

Procedure: By the procedure of Example 4, 6.13 g (60 mmol) of n-propyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 18 hours. The product was separated and then recrystallized from n-heptane to yield 2.3 g of a yellow powder product (m.p.=33°-34° C.) identified in Table I. The product was separated recrystallized from n-heptane

Conditions: temp:-1.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3.6 g of D-glucose, 2.3 g of propylurea, 0.2 g of nitroaniline and 0.1 ml of a concentrated sulphuric acid is heated at reflux for 10 minutes in 15 ml of methanol. The residue in the amount of 2.6 g is separated, added with 15 ml of glacial acetic acid, 8 ml of distilled water, 1.8 g of sodium nitrite and stirred at the temperature of -1° C. for 2 hours. The solution is evaporated, the residue is recrystallized from methanol to give 2.32 g (80% of the theoretical) of the product. M.p. 110° C. (decomposition), [α]D -5° (CH3OH), Rf =0.81. Found, %: N 14.12. Calculated, %: N 14.33. is heated The residue in the amount of 2.6 g is separated added with 15 ml of glacial acetic acid, 8 ml of distilled water, 1.8 g of sodium nitrite The solution is evaporated the residue is recrystallized from methanol to give 2.32 g (80% of the theoretical) of the product

Conditions: temp:-1.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3.6 g of D-glucose, 2.3 g of propylurea, 0.2 g of nitroaniline and 0.1 ml of a concentrated sulphuric acid is heated at reflux for 10 minutes in 15 ml of methanol. The residue in the amount of 2.6 g is separated, added with 15 ml of glacial acetic acid, 8 ml of distilled water, 1.8 g of sodium nitrite and stirred at the temperature of -1° C. for 2 hours. The solution is evaporated, the residue is recrystallized from methanol to give 2.32 g (80% of the theoretical) of the product. M.p. 110° C. (decomposition), [α]D -5° (CH3OH), Rf =0.81. Found, %: N 14.12. Calculated, %: N 14.33. is heated The residue in the amount of 2.6 g is separated added with 15 ml of glacial acetic acid, 8 ml of distilled water, 1.8 g of sodium nitrite The solution is evaporated the residue is recrystallized from methanol to give 2.32 g (80% of the theoretical) of the product

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

Procedure: This method was utilized to prepare the N-3 propylpurines. The starting material used was n-propyl urea condensed with ethyl cyanoacetate in the presence of sodium ethoxide to yield the 6-amino-1-propylpyrimidinedione in moderate yield. Commercially available 3-n-propylxanthine could also be used as the starting material.

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

Procedure: This method was utilized to prepare the N-3 propylpurines. The starting material used was n-propyl urea condensed with ethyl cyanoacetate in the presence of sodium ethoxide to yield the 6-amino-1-propylpyrimidinedione in moderate yield. Commercially available 3-n-propylxanthine could also be used as the starting material.

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

Procedure: This method was utilized to prepare the N-3 propylpurines. The starting material used was n-propyl urea condensed with ethyl cyanoacetate in the presence of sodium ethoxide to yield the 6-amino-1-propylpyrimidinedione in moderate yield. Commercially available 3-n-propylxanthine could also be used as the starting material.

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

Procedure: By the procedure of Example 4, 6.13 g (60 mmol) of n-propyl urea was reacted with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate at 140°-150° C. for 18 hours. The product was separated and then recrystallized from n-heptane to yield 2.3 g of a yellow powder product (m.p.=33°-34° C.) identified in Table I. The product was separated recrystallized from n-heptane

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

Procedure: Metallic sodium (2.6 g, 113 mmol) is added to ethanol (60 ml). The mixture is stirred until the sodium has completely finished reacting. Diethyl malonate (116 ml, 105 mmol) and n-propylurea (10 g, 98 mmol) are then added and the mixture is stirred under reflux for 5 h. After conc. HCl (5 ml) and hot water (45 ml) have been added, the mixture is filtered and the filtrate is concentrated in vacuo. Ethanol is added to the residue and the mixture is stirred. The solid is filtered off with suction and dried. under reflux for 5 h the mixture is filtered the filtrate is concentrated in vacuo Ethanol is added to the residue the mixture is stirred The solid is filtered off with suction dried

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

Procedure: Metallic sodium (2.6 g, 113 mmol) is added to ethanol (60 ml). The mixture is stirred until the sodium has completely finished reacting. Diethyl malonate (116 ml, 105 mmol) and n-propylurea (10 g, 98 mmol) are then added and the mixture is stirred under reflux for 5 h. After conc. HCl (5 ml) and hot water (45 ml) have been added, the mixture is filtered and the filtrate is concentrated in vacuo. Ethanol is added to the residue and the mixture is stirred. The solid is filtered off with suction and dried. under reflux for 5 h the mixture is filtered the filtrate is concentrated in vacuo Ethanol is added to the residue the mixture is stirred The solid is filtered off with suction dried

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

Procedure: To a solution of 47 g. (0.55 mol) cyanoacetic acid and 100 ml of acetic anhydride was added 50 g (0.49 mol) of n-propylurea. The solution was stirred at 60°-70° C. for 1 hour. After cooling, white crystals were filtered off and washed with ethanol. Yield 56.2 g (68%) (I). This was stirred in 100 ml of hot water and 60 ml of 2 N NaOH was added in portions so the solution the whole time was basic. The reaction mixture was refluxed for 20 minutes and then neutralized with 5 N HCl. After cooling, white crystals were filtered off. Yield 34.3 g (61%) (II) NMR. After cooling white crystals were filtered off washed with ethanol This was stirred in 100 ml of hot water 60 ml of 2 N NaOH was added in portions so the solution the whole time The reaction mixture was refluxed for 20 minutes After cooling white crystals were filtered off

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-cyclopropyl, N′-propylurea (1) (14.2 g, 0.1 mole), cyanoacetic acid (9.35 g, 0.11 mole) and acetic anhydride (35 ml) were mixture together and heated at 80° C. for 2 h. The solvent was then removed under reduced pressure. The residue was dissolved in MeOH (30 ml) and 20% NaOH (10 ml) was added at 4° C. The mixture was stirred at 4° C. for 1 h and then at room temperature for another 20 min. The solvent was then removed under reduced pressure and the residue was purified by silica gel column chromatography as well as C-18 column chromatography to give pure 1-propyl, 3-cyclopropyl, 6-aminouracil (1) (5.23 g, 25%). The solvent was then removed under reduced pressure The residue was dissolved in MeOH (30 ml) 20% NaOH (10 ml) was added at 4° C at room temperature for another 20 min The solvent was then removed under reduced pressure the residue was purified by silica gel column chromatography as well as C-18 column chromatography