Cl[C:2]1[C:3]2[C@H:10]([CH3:11])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:12][C@@H:13]1[NH:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1.C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1.C(OCC)(=O)C>[CH3:12][C@@H:13]1[N:18]([C:2]2[C:3]3[C@H:10]([CH3:11])[CH2:9][CH2:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:14]1
To a solution of (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (0.5 g, 3.0 mmol) in NMP (5 mL) were added (S)-tert-butyl 3-methylpiperazine-1-carboxylate (0.59 g, 3 mmol) and diisopropylethylamine (0.52 mL). The mixture was heated to 100° C. for 6 hours. The mixture was cooled and diluted with ethyl acetate (200 mL) and washed with water (6×100 mL). The organic phase was dried and concentrated. The residue was purified by silica gel chromatography, eluting with Hexane/ethyl acetate (1:1) to give (S)-tert-butyl 3-methyl-4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (0.186 g, 19%). 1H NMR (CDCl3, 400 MHz) δ 8.46 (s, 1H), 4.66 (m, 1H), 4.30-3.80 (m, 3H), 3.47 (m, 1H), 3.20 (m, 1H), 3.20-2.80 (m, 4H), 2.22 (m, 1H), 1.70 (m, 1H), 1.49 (s, 9H), 1.29 (m, 3H), 1.17 (m, 3H). MS (APCI+) [M+H] +333.
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