[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].N1([C:12](N2C=CN=C2)=[O:13])C=CN=C1.CCN(C(C)C)C(C)C.Cl.[Cl:29][C:30]1[C:35]([O:36][CH3:37])=[C:34]([O:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[N:33]=[CH:32][N:31]=1>C1COCC1>[CH2:2]([CH:3]([O:6][C:12]([N:42]1[CH2:43][CH2:44][CH:39]([O:38][C:34]2[C:35]([O:36][CH3:37])=[C:30]([Cl:29])[N:31]=[CH:32][N:33]=2)[CH2:40][CH2:41]1)=[O:13])[CH2:4][CH3:5])[CH3:1]Pentan-3-ol (0.88 g, 9.99 mmol) and di-imidazol-1-yl-methanone (1.39, 8.57 mmol) were added to THF (10 mL) and stirred at 50° C. for one hour. DIPEA (1.38 g, 10.7 mmol) and 4-chloro-5-methoxy-6-(piperidin-4-yloxy)-pyrimidine HCl (2.00 g, 7.14 mmol) were added, the vessel sealed and heated by microwave at 150° C. for one hour. Upon cooling the reaction mixture was partitioned between water and Ethyl Acetate, the organic phase washed with brine and dried with Sodium Sulfate. The crude material was purified by column chromatograph (silica gel) with 10-30% EtOAc/Hexanes to yield 1.0 grams (39%) of the desired product, as a white solid. 1HNMR (CDCl3, 400 MHz) δ 0.91 (t, J=7.83 Hz, 6H), 1.55-1.63 (m, 4H), 1.78-1.88 (m, 2H), 1.99-2.08 (m, 2H), 3.39-3.46 (m, 2H), 3.78-3.85 (m, 2H), 3.92 (s, 3H), 4.67 (m, 1H), 5.36-5.43 (m, 1H), 8.26 (s, 1H). Exact mass calculated for C16H24ClN3O4: 357.15. found: 358.3 (MH+).
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