(1R,2S)-2-methylcyclohexan-1-amine;hydrochloride

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

Procedure: Phosgene (ca. 20% in toluene, 0.9 mL) was added to a 0° C. solution of 5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine (0.300 g, 1.1 mmol) and diisopropylethylamine (0.6 mL, 3.4 mmol) in 10 mL of dichloromethane. The mixture was stirred for 10 min., then cis-2-methylcyclohexylamine hydrochloride (prepared as in Knupp, G. Chem. Ber. 1984, 117(6), 2076-98, using racemic α-methylbenzylamine) (0.249 g, 1.6 mmol) was added as a solution in 2 mL of dichloromethane with a few added drops of diisopropylethylamine. The mixture was stirred for 40 min., then concentrated to a residue. Column chromatography afforded 0.25 g (55%) of 1-(cis-2-methyl-cyclohexyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea. The mixture was stirred for 40 min. concentrated to a residue

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

Procedure: Phosgene (ca. 20% in toluene, 0.9 mL) was added to a 0° C. solution of 5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine (0.300 g, 1.1 mmol) and diisopropylethylamine (0.6 mL, 3.4 mmol) in 10 mL of dichloromethane. The mixture was stirred for 10 min., then cis-2-methylcyclohexylamine hydrochloride (prepared as in Knupp, G. Chem. Ber. 1984, 117(6), 2076-98, using racemic α-methylbenzylamine) (0.249 g, 1.6 mmol) was added as a solution in 2 mL of dichloromethane with a few added drops of diisopropylethylamine. The mixture was stirred for 40 min., then concentrated to a residue. Column chromatography afforded 0.25 g (55%) of 1-(cis-2-methyl-cyclohexyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea. The mixture was stirred for 40 min. concentrated to a residue

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

Procedure: Phosgene (ca. 20% in toluene, 0.9 mL) was added to a 0° C. solution of 5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine (0.300 g, 1.1 mmol) and diisopropylethylamine (0.6 mL, 3.4 mmol) in 10 mL of dichloromethane. The mixture was stirred for 10 min., then cis-2-methylcyclohexylamine hydrochloride (prepared as in Knupp, G. Chem. Ber. 1984, 117(6), 2076-98, using racemic α-methylbenzylamine) (0.249 g, 1.6 mmol) was added as a solution in 2 mL of dichloromethane with a few added drops of diisopropylethylamine. The mixture was stirred for 40 min., then concentrated to a residue. Column chromatography afforded 0.25 g (55%) of 1-(cis-2-methyl-cyclohexyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea. The mixture was stirred for 40 min. concentrated to a residue