[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]([C:34]1[N:39]=[CH:38][C:37]([C:40](C)(C)[O:41][SiH2]C(C)(C)C)=[CH:36][N:35]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:25])([CH3:22])([CH3:21])[CH3:20].O>C1COCC1>[C:19]([O:23][C:24]([N:26]([C:34]1[N:39]=[CH:38][C:37]([CH2:40][OH:41])=[CH:36][N:35]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:25])([CH3:20])([CH3:21])[CH3:22]Tetrabutylammonium fluoride (15.3 g, 48.6 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(ter-butyl-dimethyl-silanyloxymethyl)-pyrimidin (10.0 g, 24.3 mmol) in THF (100 mL) and stirred at room temperature overnight. Water was added and the product extracted with chloroform. The organic phase was dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 2.5:77.5) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-pyrimidin (4.20 g, 53%).
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