benzyl N-(5-aminopentyl)carbamate

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

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

Procedure: 17.84 g of the product of Step A in solution in 100 ml of methylene chloride were added to 16.4 g of 1,5-diamino-pentane in solution in 85 ml of methylene chloride and after stirring for 3 hours and concentration to dryness, the residue was chromatographed (eluant: methanol-ammonia 99-1) to obtain 10.5 g of the expected product. concentration to dryness the residue was chromatographed (eluant: methanol-ammonia 99-1)

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

Procedure: A solution of 860 mg (3.8 mmol) of 5-bromo-2,4-dichloro-pyrimidine and 1.2 ml (8.5 mmol) of triethylamine in 6 ml of acetonitrile is mixed at 0° C. with 1.0 g (3.7 mmol) of (5-amino-pentyl)-carbamic acid-benzyl ester. The reaction mixture is slowly heated to room temperature while being stirred by removal of the ice bath. After 60 hours, it is mixed with water and then extracted with ethyl acetate (2×). The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The residue that is formed is purified by chromatography (hexane/ethyl acetate 1:1). 1.2 g (2.8 mmol, corresponding to 77% of theory) of the product is obtained. extracted with ethyl acetate (2×) The combined organic phases are dried (Na2SO4) filtered concentrated by evaporation The residue that is formed is purified by chromatography (hexane/ethyl acetate 1:1) 1.2 g (2.8 mmol, corresponding to 77% of theory) of the product is obtained

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

Procedure: To a suspension of 1,5-diaminopentane dihydrochloride (2.9 g, 16.7 mmol) in THF (100 mL) was added 20% aqueous sodium hydroxide (10.0 g, 50 mmol) at 0° C. A solution of benzyl chloroformate (1.7 g, 10 mmol) in THF (10 mL) was added rapidly dropwise and the resulting mixture stirred at RT. After 1 h, the organic layer was separated and concentrated to give a residue which was dissolved in ethyl acetate (200 mL). This solution was extracted with water (3×50 mL.), dried (sodium sulfate) and concentrated. The residue was redissolved in ether (50 mL) and 1.0 ethereal hydrogen chloride (3.0 mL) was added. The resulting precipitate was filtered, suspended in CH2Cl2 (75 mL) and shaken with 5% sodium hydroxide (15 mL). The organic layer was washed with water (75 mL), dried (sodium sulfate) and concentrated to give the title compound 0.25 g, 30%): 1H NMR (400 MHz, CDCl3) δ7.15-7.4 (m, 5H), 5.15-5.4 (m, 1H), 5.05 (s, 2H), 3.05-3.2 (m, 2H), 2.55-2.7 (m, 2H), 1.2-1.5 (m, 6H). the organic layer was separated concentrated to give a residue which This solution was extracted with water (3×50 mL.) dried (sodium sulfate) concentrated The residue was redissolved in ether (50 mL) 1.0 ethereal hydrogen chloride (3.0 mL) was added The resulting precipitate was filtered shaken with 5% sodium hydroxide (15 mL) The organic layer was washed with water (75 mL) dried (sodium sulfate) concentrated

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

Procedure: 17.84 g of the product of Step A in solution in 100 ml of methylene chloride were added to 16.4 g of 1,5-diamino-pentane in solution in 85 ml of methylene chloride and after stirring for 3 hours and concentration to dryness, the residue was chromatographed (eluant: methanol-ammonia 99-1) to obtain 10.5 g of the expected product. concentration to dryness the residue was chromatographed (eluant: methanol-ammonia 99-1)

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

Procedure: A solution of 860 mg (3.8 mmol) of 5-bromo-2,4-dichloro-pyrimidine and 1.2 ml (8.5 mmol) of triethylamine in 6 ml of acetonitrile is mixed at 0° C. with 1.0 g (3.7 mmol) of (5-amino-pentyl)-carbamic acid-benzyl ester. The reaction mixture is slowly heated to room temperature while being stirred by removal of the ice bath. After 60 hours, it is mixed with water and then extracted with ethyl acetate (2×). The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The residue that is formed is purified by chromatography (hexane/ethyl acetate 1:1). 1.2 g (2.8 mmol, corresponding to 77% of theory) of the product is obtained. extracted with ethyl acetate (2×) The combined organic phases are dried (Na2SO4) filtered concentrated by evaporation The residue that is formed is purified by chromatography (hexane/ethyl acetate 1:1) 1.2 g (2.8 mmol, corresponding to 77% of theory) of the product is obtained