F[C:2](F)(F)[C:3](O)=[O:4].[N:8]1[CH:13]=[CH:12][CH:11]=[N:10][C:9]=1[NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:41]=[CH:40][C:21]([C:22]([NH:24][CH2:25][C@H:26]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])[C:27]([OH:29])=[O:28])=[O:23])=[CH:20][CH:19]=1>C(O)(=O)C.Cl.[Pd]>[CH3:2][CH2:3][OH:4].[NH4+:8].[OH-:17].[OH2:4].[N:8]1[CH2:13][CH2:12][CH2:11][NH:10][C:9]=1[NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:24][CH2:25][C@H:26]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])[C:27]([OH:29])=[O:28])=[O:23])=[CH:40][CH:41]=1Pyrimidine 19-8 (1.05 g, 1.75 mmol) was dissolved in a mixture of acetic acid (50 mL) and conc HCl (4.5 mL). After addition of 10% Pd/C (450 mg) the mixture was shaken on a Parr hydrogenator under 45 psi H2 pressure for 2 h. The reaction mixture was filtered, concentrated, azeotroped with toluene, and purified by flash chromatography (silica 20:1:1 then 8:1:1 EtOH/NH4OH/H2O) providing 19-9 as a white solid.
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