C([O:9][CH2:10][C:11]1[C:12]2[N:20]=[C:19]([CH:21]3[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]3)[S:18][C:13]=2[N:14]=[C:15]([CH3:17])[N:16]=1)(=O)C1C=CC=CC=1.O(C)[Na].Cl.CCOC(C)=O>CO>[CH3:27][C:24]1([CH3:28])[CH2:23][CH2:22][CH:21]([C:19]2[S:18][C:13]3[N:14]=[C:15]([CH3:17])[N:16]=[C:11]([CH2:10][OH:9])[C:12]=3[N:20]=2)[CH2:26][CH2:25]1To a mixture of [2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methyl benzoate (13.8 g) and MeOH (250 mL) was added a 28% NaOCH3 solution (670 μL) in MeOH, followed by stirring at room temperature for 3 hours. The reaction mixture was neutralized by the addition of 4 M HCl/EtOAc (870 μL), and concentrated under reduced pressure. To the residue was added water, followed by extraction with EtOAc. To the organic layer were added MgSO4 and basic silica gel, followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure. The residue was purified by silica gel column (hexane/EtOAc) to obtain [2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methanol (7.9 g).
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