Tetrabutylammonium Fluoride → HCID 68515826, compound

HRID 1513076Notes

Reaction equation

HRID 1513076 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[C:17]([O:18][CH2:19][C:20]2[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=2[F:28])=[CH:16][C:15]([N:29]2[C:37](=[O:38])[NH:36][C:35]3[C:30]2=[N:31][C:32]([CH:41]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[N:33][C:34]=3[O:39][CH3:40])=[C:14]([Cl:52])[CH:13]=1)(C(C)(C)C)(C)C.[Si](OCCOC1C(OCC2C(OC)=CC=CC=2F)=CC(N)=C(Cl)C=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:52][C:14]1[CH:13]=[C:12]([O:11][CH2:10][CH2:9][OH:8])[C:17]([O:18][CH2:19][C:20]2[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=2[F:28])=[CH:16][C:15]=1[N:29]1[C:37](=[O:38])[NH:36][C:35]2[C:30]1=[N:31][C:32]([CH:41]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:47]([O:49][CH2:50][CH3:51])=[O:48])=[N:33][C:34]=2[O:39][CH3:40]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 59309701HCID 59309701, compoundHCID 68513905HCID 68513905, compound

Product 1

HCID 68515826HCID 68515826, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9-{-4-[2-(tert-butyldimethylsilyloxy)ethoxy]-2-chloro-5-(2-fluoro-6-methoxybenzyloxy)phenyl}-2-bis(ethoxycarbonyl)methyl-6-methoxy-7,9-dihydro-8H-purin-8-one (0.32 g), which was prepared in a similar manner to that described in Example 310 using 4-[2-(tert-butyldimethylsilyloxy)ethoxy]-2-chloro-5-(2-fluoro-6-methoxy-benzyloxy)aniline instead of 2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyaniline, in tetrahydrofuran (4.2 mL) was added tetra(n-butyl)ammonium fluoride (1 mol/L tetrahydrofuran solution, 8.4 mL), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-ethyl acetate/methanol=9/1) to give 9-[2-chloro-5-(2-fluoro-6-methoxybenzyloxy)-4-(2-hydroxyethoxy)-phenyl]-2-bis(ethoxycarbonyl)methyl-6-methoxy-7,9-dihydro-8H-purin-8-one (0.24 g). To this material were added tetrahydrofuran (7 mL), methanol (3.5 mL), water (3.5 mL) and lithium hydroxide monohydrate (0.31 g), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate−ethyl acetate/methanol=7/3) to give the title compound (0.14 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-afa674a93ac14f6bae89730e90d88cac
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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