[(1R,2S)-2-aminocyclohexyl]methanol

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

Procedure: The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using rac-[(1R,2S)-2-aminocyclohexyl]methanol instead of cyclopentanamine. The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1), and then the final product was washed with diethyl ether to afford the titled compound as a white solid. 1H NMR (400 MHz, methanol-d6) δ ppm 1.35 (bs, 2H), 1.50 (bs, 6H), 1.89 (bs, 3H), 2.20 (bs, 3H), 3.40-3.48 (m, 1H), 3.60-3.68 (m, 1H), 4.10-4.18 (m, 1H), 4.64 (bs, 2H), 7.26 (t, J=5.64 Hz, 1H), 7.40 (d, J=8.06 Hz, 1H), 7.75 (d, J=7.79 Hz, 1H), 8.46 (d, J=4.83, 1H); MS (ESI) m/z 342.8 (M+1)+. The titled compound was synthesized The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1) the final product was washed with diethyl ether

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

Procedure: The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using rac-[(1R,2S)-2-aminocyclohexyl]methanol instead of cyclopentanamine. The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1), and then the final product was washed with diethyl ether to afford the titled compound as a white solid. 1H NMR (400 MHz, methanol-d6) δ ppm 1.35 (bs, 2H), 1.50 (bs, 6H), 1.89 (bs, 3H), 2.20 (bs, 3H), 3.40-3.48 (m, 1H), 3.60-3.68 (m, 1H), 4.10-4.18 (m, 1H), 4.64 (bs, 2H), 7.26 (t, J=5.64 Hz, 1H), 7.40 (d, J=8.06 Hz, 1H), 7.75 (d, J=7.79 Hz, 1H), 8.46 (d, J=4.83, 1H); MS (ESI) m/z 342.8 (M+1)+. The titled compound was synthesized The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1) the final product was washed with diethyl ether

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The hydrazide of (1S,2R)-2-hydroxymethyl-1-cyclohexanecarboxylic acid (0.5 gram) is reacted with a solution of 0.5 grams of sodium nitrite in 10 ml of 5% H2SO4. The reaction mixture is maintained for 1 hour at 0-5° C., followed extraction of the reaction mixture with ethyl acetate, followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether, drying of the extracts over MgSO4, filtration, and the removal of solvent by rotary evaporation. The product (1S,2R)-1-amino-2-(hydroxymethyl)cyclohexane is isolated as a light yellow oil. extraction of the reaction mixture with ethyl acetate followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether drying of the extracts over MgSO4, filtration the removal of solvent by rotary evaporation

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The hydrazide of (1S,2R)-2-hydroxymethyl-1-cyclohexanecarboxylic acid (0.5 gram) is reacted with a solution of 0.5 grams of sodium nitrite in 10 ml of 5% H2SO4. The reaction mixture is maintained for 1 hour at 0-5° C, followed extraction of the reaction mixture with ethyl acetate, followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether, drying of the extracts over MgSO4, filtration, and the removal of solvent by rotary evaporation. The product (1S,2R)-1-amino-2-(hydroxymethyl)cyclohexane is isolated as a light yellow extraction of the reaction mixture with ethyl acetate followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether drying of the extracts over MgSO4, filtration the removal of solvent by rotary evaporation

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

Procedure: The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using rac-[(1R,2S)-2-aminocyclohexyl]methanol instead of cyclopentanamine. The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1), and then the final product was washed with diethyl ether to afford the titled compound as a white solid. 1H NMR (400 MHz, methanol-d6) δ ppm 1.35 (bs, 2H), 1.50 (bs, 6H), 1.89 (bs, 3H), 2.20 (bs, 3H), 3.40-3.48 (m, 1H), 3.60-3.68 (m, 1H), 4.10-4.18 (m, 1H), 4.64 (bs, 2H), 7.26 (t, J=5.64 Hz, 1H), 7.40 (d, J=8.06 Hz, 1H), 7.75 (d, J=7.79 Hz, 1H), 8.46 (d, J=4.83, 1H); MS (ESI) m/z 342.8 (M+1)+. The titled compound was synthesized The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1) the final product was washed with diethyl ether