Trifluoroacetic acid → 2-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (27.4 g) was slowly added to a suspension of the product from step (iii) (105.0 g) and n-pentylamine (62.9 g) in butyl acetate (877.8 g) and the mixture was heated at 120° C. for 2 hours. The mixture was cooled to 20° C. and 4% aq. NaOH (997.5 g) was added to the mixture. The organic layer was separated, washed with water (997.5 g) and 10% aq. NH4Cl (997.5 g) respectively and the solvent evaporated under reduced pressure to afford a solid. The solid was dissolved in acetonitrile (221.1 g) at 50° C. and the solution was cooled to 42° C., seeded and stirred at this temperature for 1 hour. After the mixture was cooled to 5° C. and stirred at 5° C. for 1 hour, the resulting precipitate was collected by filtration, washed with acetonitrile (2×31.5 g) and dried under reduced pressure to give the subtitle compound as a solid, 52.0 g; 1H NMR DMSO-d6: δ 7.23 (d, 2H), 7.11 (d, 2H), 6.17 (t, 1H), 5.68 (s, 2H), 3.96 (s, 2H), 3.73 (s, 2H), 3.27-3.22 (m, 2H), 2.00 (s, 3H), 1.47-1.40 (m, 2H), 1.28-1.19 (m, 2H), 1.17-1.09 (m, 2H), 0.82 (t, 3H).

Provenance & Evidence