The mixture of 4-amino-2-(4-amino-2-hydroxybutoxy)benzonitrile, 2 TFA salt (Preparation Z, 50 mg, 0.111 mmol), 2,4-dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (Preparation R, 31.5 mg, 0.111 mmol) and N-ethyl-N-isopropylpropan-2-amine (97 μL, 0.556 mmol) in acetonitrile (556 μL) was stirred at rt for 24 h. The reaction mixture was concentrated and purified by Prep-HPLC to obtain 4-amino-2-(4-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)-2-hydroxybutoxy)benzonitrile, TFA (14.73 mg, 22.75% yield). LC-MS (M+H)+=468.2. 1H NMR (500 MHz, methanol-d4) δ 7.27-7.15 (m, 3H), 7.14-7.01 (m, 2H), 6.40-6.24 (m, 2H), 4.44-4.33 (m, 1H), 4.17-4.04 (m, 2H), 4.03-3.95 (m, 1H), 3.89-3.66 (m, 2H), 2.94-2.81 (m, 1H), 2.81-2.67 (m, 2H), 2.14 (td, J=7.5, 4.0 Hz, 1H), 2.10-2.00 (m, 1H), 1.95 (dd, J=14.0, 6.4 Hz, 1H).
