Tributylstannane → 9-[4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-9H-purin-6-ylamine

HRID 1893162Notes

Reaction equation

HRID 1893162 reaction equation
C1(OC(=S)O[CH:10]2[CH:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:26][SiH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])([CH:23]=[CH2:24])[O:12][CH:11]2[N:44]2[CH:52]=[N:51][C:50]3[C:45]2=[N:46][CH:47]=[N:48][C:49]=3[NH2:53])C=CC=CC=1.C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[CH2:16]([O:15][CH:14]1[C:13]([C:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:26][SiH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])([CH:23]=[CH2:24])[O:12][CH:11]([N:44]2[CH:52]=[N:51][C:50]3[C:45]2=[N:46][CH:47]=[N:48][C:49]=3[NH2:53])[CH2:10]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 131730812Thiocarbonic acid O-[2-(6-amino-purin-9-yl)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-3-yl]ester O-phenyl ester

Product 1

HCID 1317308139-[4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-9H-purin-6-ylamineYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask was added Thiocarbonic acid O-[2-(6-amino-purin-9-yl)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-3-yl]ester O-phenyl ester, toluene, tributyl tin hydride, and AIBN. The reaction was stirred at reflux, cooled back to room temperature, was extracted, and the solvent was removed to provide the titled compound in 90% yield.

Workup

  1. temperatureat reflux
  2. extractionwas extracted
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-a8bbdec765a84e888e9771077e2ecb70
Source dataset
uspto-grants-2013_08
Patent number
US08513214B2

Reaction notes

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