[OH:1][C:2]1[N:7]=[C:6](SC)[N:5]=[C:4]([CH2:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21]([OH:23])=[O:22])=[CH:16][CH:15]=[CH:14]3)[CH:3]=1>[Ni].CCO.O>[OH:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21]([OH:23])=[O:22])=[CH:16][CH:15]=[CH:14]3)[CH:3]=129 g Raney Nickel in EtOH are added to a solution of 5.08 mMol 6-(6-hydroxy-2-methylsulfanyl-pyrimidin-4-ylmethyl)-naphthalene-1-carboxylic acid in 220 ml EtOH and 170 ml water. The mixture is stirred for 3.5 h at 80° C., filtered hot and the residue is extensively washed with EtOH/H2O 1:1. Partial concentration in vacuo, acidification of the residue with 1 N HCl (pH=1), filtration of the precipitated product, washing with 50 ml 0.1 N HCl and drying (HV; 90° C.) gives the title compound. Additional product can be isolated from the filtrate by extraction with 3 Portions of EtOAc, washing of the organic layers with brine, drying (Na2SO4), concentration and chromatography (Combi Flash; CH2Cl2→CH2Cl2/MeOH+0.5% HOAc 19:1): TLC (CH2Cl2/MeOH+0.5% HOAc 9:1): Rf=0.17.
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