[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:10]=[C:11]([O:28]C)[C:12]2[CH2:18][N:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[CH:20]=3)[CH2:16][CH2:15][C:13]=2[N:14]=1.Cl.O.C([O-])(O)=O.[Na+]>CCO>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[N:10]=[C:11]([OH:28])[C:12]2[CH2:18][N:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([CH:25]([CH3:26])[CH3:27])[CH:20]=3)[CH2:16][CH2:15][C:13]=2[N:14]=1To a solution of 2-(2,6-dimethylphenyl)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (3.3 g, 8.51 mmol) in EtOH (30 mL) in a 150 mL sealed tube was added concentrated hydrochloride (21 mL). The tube was sealed, stirred, and heated at 90° C. for 16 h. The reaction mixture was cooled to r.t. and poured onto iced-water. Solid NaHCO3 was added to neutralize the mixture. The mixture was extracted by DCM three times. The combined organic layers were dried over Na2SO4. After filtration and concentration, the resulting residue was purified via silica gel FCC (0-100% EtOAc/heptane) to give 2-(2,6-dimethylphenyl)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol. 1H NMR (400 MHz, CD2Cl2) δ ppm 9.95 (br. s., 1 H), 7.21-7.36 (m, 1 H), 7.13 (d, J=7.3 Hz, 2 H), 5.76 (s, 1 H), 3.87 (s, 2 H), 3.68 (s, 3 H), 3.22 (t, J=5.7 Hz, 2 H), 2.77-2.97 (m, 3 H), 2.22 (s, 6 H), 1.22 (d, J=7.1 Hz, 6 H). MS (ESI+) m/z 378.3 (M+H)+.
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