[CH3:1][C:2]([N:5]1[C:9]([NH2:10])=[C:8]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([O:18]CC3C=CC=CC=3)[C:12]=2[O:26][CH3:27])[C:7]([CH3:28])=[N:6]1)([CH3:4])[CH3:3].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>C1COCC1.C(OCC)(=O)C.[Pd]>[NH2:10][C:9]1[N:5]([C:2]([CH3:3])([CH3:4])[CH3:1])[N:6]=[C:7]([CH3:28])[C:8]=1[C:11]1[C:12]([O:26][CH3:27])=[C:13]([OH:18])[CH:14]=[C:15]([F:17])[CH:16]=1A solution of 1-(1,1-dimethylethyl)-4-(5-fluoro-2-(methyloxy)-3-[{phenylmethyl)oxy]phenyl}-3-methyl-1H-pyrazol-5-amine (25 g, 0.0652 mol) in a mixture of THF-ethyl acetate (1:1, 300 mL) was hydrogenated over 10% Pd—C (2.5 g) at 40 Psi for 2 h. The catalyst was filtered off, and the filtrate was concentrated. The resulting crude was triturated with diethyl ether; a white solid was precipitated. It was collected by filtration, washed with an additional portion of diethyl ether and dried in vacuo to give 17.8 g of 3-[5-amino-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-4-yl]-5-fluoro-2-(methyloxy)phenol (93%). 1H NMR (400 MHz, DMSO-d6): δ 9.63 (s, 1H), 6.56 (dd, 1H), 6.38 (dd, 1H), 4.44 (s, 2H), 3.37 (s, 3H), 1.98 (s, 3H), 1.56 (s, 9H); MS (EI) for C15H20FN3O2: 294 (MH+)
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