Methanol → Trifluoroacetic acid

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To a solution of 2-chloro-N-methyl-7-(6-(trifluoromethyl)pyridin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (Preparation AZa) (8 mg, 0.024 mmol) and 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (4.97 mg, 0.024 mmol) in NMP (Volume: 48.7 μl) was added H2SO4 (1.686 0.032 mmol). The reaction mixture was stirred at 100° C. in a capped vial overnight. The reaction mixture was diluted with methanol and purified by reverse-phase preparative HPLC to afford N2-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-N4-methyl-7-(6-(trifluoromethyl)pyridin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine, TFA (6.3 mg, 10.22 μmol, 42.0% yield). LC-MS (M+H)+=497.1. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 11.69 (1H, s), 9.32 (1H, s), 8.63 (1H, s), 7.94 (1H, d, J=6.7 Hz), 7.72-7.79 (2H, m), 7.59 (1H, s), 7.52 (1H, dd, J=8.7, 1.7 Hz), 5.79 (1H, d, J=4.9 Hz), 4.60-4.63 (1H, m), 3.99 (3H, s), 3.28 (3H, m), 2.97-3.01 (1H, m), 2.84-2.91 (2H, m), 2.64 (3H, s), 2.33-2.39 (1H, m), 1.27-1.33 (1H, m).

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