Cl[CH2:2][C:3]1[NH:4][C:5](=[O:13])[C:6]2[CH2:12][O:11][CH2:10][CH2:9][C:7]=2[N:8]=1.CCN(C(C)C)C(C)C.[CH:23]1([CH2:26][NH2:27])[CH2:25][CH2:24]1>CCO>[CH:23]1([CH2:26][NH:27][CH2:2][C:3]2[NH:4][C:5](=[O:13])[C:6]3[CH2:12][O:11][CH2:10][CH2:9][C:7]=3[N:8]=2)[CH2:25][CH2:24]1To a solution of 2-chloromethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (1 g, 5 mmol, 1 eq.) and DIEA (4.35 mL, 24.9 mmol, 5 eq.) in 7 mL of EtOH was added cyclopropylmethylamine (1.4 g, 20 mmol, 4 eq.). The resulting mixture was heated at 65° C. overnight. After 18 h, the reaction mixture was concentrated in vacuo to give an oil that was purified by silica gel column chromatography (100% CH2Cl2) to give the title compound as a white solid (0.23 g, 20%). 1H NMR (400 MHz, chloroform-d) δ ppm 4.37-4.42 (m, 2H), 3.95 (s, 1H), 3.80-3.88 (m, 3H), 2.63-2.72 (m, 1H), 2.54-2.63 (m, 3H), 0.89-1.05 (m, 1H), 0.42-0.54 (m, 2H), 0.14-0.26 (m, 2H). Exact mass calculated for C12H18N3O2 236.1. MS (ESI) m/z 236.9 (M+H)+. Retention time: 0.56 min (5-95% CH3CN/H2O over 2 min with 0.1% formic acid, Inertsil 3×3 mm C-8-3 column with flow rate of 2 mL/min).
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