HCID 57474807, compound → HCID 57474812, compound

HRID 391702Notes

Reaction equation

HRID 391702 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]=[C:15]3[C:11]([NH:12][C:13](=[O:23])[N:14]3[CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:10]([C:24]([O:26]C)=O)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Si](OC1C=C(C2N=C3C(NC(=O)N3C3CCOCC3)=C(C(OC)=O)[N:53]=2)C=CC=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]=[C:15]3[C:11]([NH:12][C:13](=[O:23])[N:14]3[CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:10]([C:24]([NH2:53])=[O:26])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 57474807HCID 57474807, compoundHCID 67147884HCID 67147884, compound

Product 1

HCID 57474812HCID 57474812, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

Methyl 2-(3-hydroxyphenyl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylate. Methyl 2-(3-(tert-butyldiphenylsilyloxy)phenyl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylate (0.270 g, 0.513 mmol) was dissolved in tetrahyrdrofuran (10 mL) and tetrabutylammonium fluoride on silica gel (0.410 g, 0.615 mmol) was added to the solution. The solution stirred at ambient temperature for two hours. LCMS confirms product and no starting materials. The solution was filtered and condensed to give the crude title compound (0.110 g, 58%) which is used in the next step without further purification or characterization.

Workup

  1. additionwas added to the solution
  2. filtrationThe solution was filtered
  3. customcondensed

Sources & evidence

ORD record
ord-001e5197acf14e1aac26fa5f8e9ce3f3
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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