4-methoxybutan-1-amine

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

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

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

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

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

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

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

Procedure: 2-Chloro-6-(4-methoxybutylamino)-9-cyclopentylpurine is prepared from 2,6-dichloro-9-cyclopentylpurine, 4-methoxybutylamine, and triethylamine essentially as described above in Example 1, Scheme A, step b.

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

Procedure: Combined 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (50 mg, 0.156 mmol) and 4-methoxybutan-1-amine (29.0 mg, 0.281 mmol) in DMF (1 mL). Then added a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (50 mg, 0.261 mmol) and triethylamine (0.121 mL, 0.868 mmol) in DMF (0.5 mL), and a solution of HOBT (35 mg, 0.259 mmol) in DMF (0.5 mL). The mixture was then stirred overnight at room temperature. Into the reaction mixture was then poured 20 mL of saturated ammonium chloride solution and was rigorously stirred for 1 hour to give a solid. The solid was collected on by filtration, washed three times with saturated ammonium chloride solution, and then twice with ether, before being dried to give the title compound (49 mg, 77% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50-1.61 (m, 4 H) 2.42 (s, 3 H) 3.23 (s, 3 H) 3.25-3.45 (m, 8 H) 7.42-7.47 (m, 1 H) 7.49 (s, 1 H) 7.80 (s, 1 H) 8.19 (dd, J=8.72, 2.40 Hz, 1 H) 8.27 (d, J=8.34 Hz, 1 H) 8.49-8.57 (m, 2 H) 8.83 (d, J=2.02 Hz, 1 H). MS m/z [M+H]+ 406.2. was rigorously stirred for 1 hour to give a solid The solid was collected on by filtration washed three times with saturated ammonium chloride solution twice with ether, before being dried

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

Procedure: Combined 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (50 mg, 0.156 mmol) and 4-methoxybutan-1-amine (29.0 mg, 0.281 mmol) in DMF (1 mL). Then added a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (50 mg, 0.261 mmol) and triethylamine (0.121 mL, 0.868 mmol) in DMF (0.5 mL), and a solution of HOBT (35 mg, 0.259 mmol) in DMF (0.5 mL). The mixture was then stirred overnight at room temperature. Into the reaction mixture was then poured 20 mL of saturated ammonium chloride solution and was rigorously stirred for 1 hour to give a solid. The solid was collected on by filtration, washed three times with saturated ammonium chloride solution, and then twice with ether, before being dried to give the title compound (49 mg, 77% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50-1.61 (m, 4H) 2.42 (s, 3H) 3.23 (s, 3H) 3.25-3.45 (m, 8H) 7.42-7.47 (m, 1H) 7.49 (s, 1H) 7.80 (s, 1H) 8.19 (dd, J=8.72, 2.40 Hz, 1H) 8.27 (d, J=8.34 Hz, 1H) 8.49-8.57 (m, 2H) 8.83 (d, J=2.02 Hz, 1H). MS m/z [M+H]+ 406.2. was rigorously stirred for 1 hour to give a solid The solid was collected on by filtration washed three times with saturated ammonium chloride solution twice with ether, before being dried

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

Procedure: 2-Chloro-6-(4-methoxybutylamino)-9-cyclopentylpurine is prepared from 2,6-dichloro-9-cyclopentylpurine, 4-methoxybutylamine, and triethylamine essentially as described above in Example 1, Scheme A, step b.

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

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