Stannanecarbonitrile, tributyl- → (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate

HRID 1724638Notes

Reaction equation

HRID 1724638 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17](I)=[N:18][C:19]=3[NH:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[O:7][C@@H:6]1[CH2:30][O:31][C:32](=[O:34])[CH3:33])(=[O:3])[CH3:2].C([Sn]([C:48]#[N:49])(CCCC)CCCC)CCC>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:4][C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([C:48]#[N:49])=[N:18][C:19]=3[NH:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[O:7][C@@H:6]1[CH2:30][O:31][C:32](=[O:34])[CH3:33])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 200512Stannanecarbonitrile, tributyl-HCID 14886862(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate

Product 1

HCID 58767046(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetateYield 87.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate (0.9 g, 1.53 mmol) in N,N-dimethylformamide (40 ml) was added tributyltin cyanide (0.58 g, 1.84 mmol) and tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol), and the mixture was stirred at 120° C. f overnight. Solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate and filtered through celite. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel, eluting with a mixture of ethanol/hexane 1:1, to provide (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate (0.65 g).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. filtrationfiltered through celite
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was chromatographed on silica gel
  6. washeluting with a mixture of ethanol/hexane 1:1

Sources & evidence

ORD record
ord-0c5a7ae89be54a569321ec85d3be16e4
Source dataset
uspto-grants-2009_02
Patent number
US07488720B2

Reaction notes

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