4,5-Difluoro-2-methylaniline

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 (4,5-difluoro-2-methylphenyl)amine 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 (300 MHz, DMSO-d6) δ ppm 2.02 (s, 3H), 2.06 (s, 3H), 2.16 (s, 3H), 4.34 (bs, 2H), 6.81 (bs, 1H), 7.07-7.41 (m, 4H), 7.56 (bs, 1H), 7.63 (d, J=7.3 Hz, 1H), 8.42 (d, J=4.2 Hz, 1H); MS (ESI) m/z 356.6 (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 (4,5-difluoro-2-methylphenyl)amine 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 (300 MHz, DMSO-d6) δ ppm 2.02 (s, 3H), 2.06 (s, 3H), 2.16 (s, 3H), 4.34 (bs, 2H), 6.81 (bs, 1H), 7.07-7.41 (m, 4H), 7.56 (bs, 1H), 7.63 (d, J=7.3 Hz, 1H), 8.42 (d, J=4.2 Hz, 1H); MS (ESI) m/z 356.6 (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 (4,5-difluoro-2-methylphenyl)amine 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 (300 MHz, DMSO-d6) δ ppm 2.02 (s, 3H), 2.06 (s, 3H), 2.16 (s, 3H), 4.34 (bs, 2H), 6.81 (bs, 1H), 7.07-7.41 (m, 4H), 7.56 (bs, 1H), 7.63 (d, J=7.3 Hz, 1H), 8.42 (d, J=4.2 Hz, 1H); MS (ESI) m/z 356.6 (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