Triacetoxyperiodinane → HCID 87481323, compound

HRID 1513069Notes

Reaction equation

HRID 1513069 reaction equation
[Cl:1][C:2]1[C:7](C)=[C:6](O)[C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[CH:4][C:3]=1[N:22]1[C:30](=[O:31])[NH:29][C:28]2[C:23]1=[N:24][C:25]([CH3:34])=[N:26][C:27]=2[O:32][CH3:33].C[C:36](OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=[O:37]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH:36]=[O:37])[C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[CH:4][C:3]=1[N:22]1[C:30](=[O:31])[NH:29][C:28]2[C:23]1=[N:24][C:25]([CH3:34])=[N:26][C:27]=2[O:32][CH3:33]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 87508639HCID 87508639, compound

Product 1

HCID 87481323HCID 87481323, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-hydroxy-methylphenyl]-6-methoxy-2-methyl-7,9-dihydro-8H-purin-8-one (11 mg) in methylene chloride (2 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (19 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/2−1/3) to give 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-formylphenyl]-6-methoxy-2-methyl-7,9-dihydro-8H-purin-8-one (9 mg). To this material were added tert-butanol (1 mL), water (0.5 mL), tetrahydrofuran (1 mL), sodium dihydrogen phosphate (4 mg), 2-methyl-2-butene (0.006 mL) and sodium chlorite (6 mg) successively, and the mixture was stirred at 30° C. for 3 hours. 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 sodium sulfate, and the solvent was removed under reduced pressure. The residual crystals were suspended in a mixed solvent (n-hexane/ethyl acetate=3/1), and collected by filtration. The collected crystals were dried under reduced pressure to give the title compound (4 mg).

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/2−1/3)

Sources & evidence

ORD record
ord-b36e81bb60f94dd5954bff5059c28a1a
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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